Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'J. Woollins' 'Petr Kilian' 'A. Slawin' _publ_contact_author_name 'J. Woollins' _publ_contact_author_address ; Department of Chemistry University of St Andrews St Andrews FIFE SCOTLAND KY16 9ST UNITED KINGDOM ; _publ_contact_author_email JDW3@ST-ANDREWS.AC.UK _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Preparation and structures of 1,2-dihydro-1,2-diphosphaacenaphthenes and rigid backbone stabilised triphosphenium cation ; # Attachment '2.CIF' data_2 _database_code_depnum_ccdc_archive 'CCDC 291570' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H26 I N P3.C2 H3 N. I' _chemical_formula_sum 'C36 H29 I N P3' _chemical_formula_weight 695.41 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.1574(17) _cell_length_b 12.0357(15) _cell_length_c 20.222(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.823(2) _cell_angle_gamma 90.00 _cell_volume 3095.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 222 _cell_measurement_theta_min 12 _cell_measurement_theta_max 28 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max .1 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 1.216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8932 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details - _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16711 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0137 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.40 _reflns_number_total 5623 _reflns_number_gt 5166 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0312P)^2^+2.3734P] 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 SHELXL _refine_ls_extinction_coef 0.00065(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5623 _refine_ls_number_parameters 372 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0263 _refine_ls_R_factor_gt 0.0231 _refine_ls_wR_factor_ref 0.0603 _refine_ls_wR_factor_gt 0.0581 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.855636(11) 0.946256(12) 0.159322(7) 0.03159(6) Uani 1 1 d . . . P1 P 0.66941(4) 1.01620(4) 0.37954(2) 0.01911(11) Uani 1 1 d . . . P19 P 0.55554(4) 1.06106(4) 0.43213(3) 0.02248(11) Uani 1 1 d . . . C1 C 0.74250(14) 1.13188(15) 0.35818(9) 0.0193(4) Uani 1 1 d . . . C2 C 0.77049(15) 1.12303(17) 0.29708(10) 0.0244(4) Uani 1 1 d . . . H2A H 0.7486 1.0599 0.2689 0.029 Uiso 1 1 calc R . . C3 C 0.83086(16) 1.20569(18) 0.27568(10) 0.0277(4) Uani 1 1 d . . . H3A H 0.8491 1.1982 0.2334 0.033 Uiso 1 1 calc R . . C4 C 0.86295(15) 1.29635(17) 0.31581(11) 0.0260(4) Uani 1 1 d . . . H4A H 0.9046 1.3514 0.3016 0.031 Uiso 1 1 calc R . . C5 C 0.83511(14) 1.30977(16) 0.37857(10) 0.0216(4) Uani 1 1 d . . . C6 C 0.86964(15) 1.40581(17) 0.41843(11) 0.0261(4) Uani 1 1 d . . . H6A H 0.9124 1.4586 0.4032 0.031 Uiso 1 1 calc R . . C7 C 0.84258(16) 1.42375(17) 0.47829(12) 0.0296(5) Uani 1 1 d . . . H7A H 0.8668 1.4882 0.5048 0.036 Uiso 1 1 calc R . . C8 C 0.77865(16) 1.34640(17) 0.50056(10) 0.0271(4) Uani 1 1 d . . . H8A H 0.7578 1.3607 0.5414 0.032 Uiso 1 1 calc R . . C9 C 0.74522(14) 1.24968(16) 0.46436(10) 0.0219(4) Uani 1 1 d . . . C10 C 0.77265(13) 1.22740(15) 0.40132(9) 0.0184(4) Uani 1 1 d . . . P9 P 0.66683(4) 1.15766(4) 0.50321(2) 0.02221(11) Uani 1 1 d . . . C11 C 0.59687(16) 0.94517(16) 0.30303(10) 0.0237(4) Uani 1 1 d . . . C12 C 0.64761(17) 0.86658(19) 0.27181(11) 0.0328(5) Uani 1 1 d . . . H12A H 0.7210 0.8545 0.2890 0.039 Uiso 1 1 calc R . . C13 C 0.59134(19) 0.8060(2) 0.21579(12) 0.0378(5) Uani 1 1 d . . . H13A H 0.6262 0.7536 0.1942 0.045 Uiso 1 1 calc R . . C14 C 0.48467(18) 0.82274(19) 0.19187(11) 0.0351(5) Uani 1 1 d . . . H14A H 0.4455 0.7797 0.1546 0.042 Uiso 1 1 calc R . . C15 C 0.43436(18) 0.9013(2) 0.22156(11) 0.0334(5) Uani 1 1 d . . . H15A H 0.3609 0.9128 0.2041 0.040 Uiso 1 1 calc R . . C16 C 0.48980(17) 0.96408(18) 0.27690(11) 0.0275(4) Uani 1 1 d . . . H16A H 0.4549 1.0192 0.2966 0.033 Uiso 1 1 calc R . . C17 C 0.76487(15) 0.91554(16) 0.42424(10) 0.0244(4) Uani 1 1 d . . . C18 C 0.87197(16) 0.93316(18) 0.43973(11) 0.0297(5) Uani 1 1 d . . . H18A H 0.8995 0.9980 0.4239 0.036 Uiso 1 1 calc R . . C19 C 0.93954(17) 0.8547(2) 0.47898(12) 0.0373(5) Uani 1 1 d . . . H19A H 1.0133 0.8666 0.4899 0.045 Uiso 1 1 calc R . . C20 C 0.90067(18) 0.7610(2) 0.50191(13) 0.0396(5) Uani 1 1 d . . . H20A H 0.9471 0.7097 0.5301 0.048 Uiso 1 1 calc R . . C21 C 0.79346(19) 0.7412(2) 0.48391(13) 0.0396(5) Uani 1 1 d . . . H21A H 0.7665 0.6746 0.4981 0.048 Uiso 1 1 calc R . . C22 C 0.72617(17) 0.81789(18) 0.44546(12) 0.0339(5) Uani 1 1 d . . . H22A H 0.6526 0.8042 0.4333 0.041 Uiso 1 1 calc R . . C23 C 0.58907(16) 1.24628(17) 0.54345(11) 0.0272(4) Uani 1 1 d . . . C24 C 0.51352(18) 1.31470(18) 0.50177(12) 0.0329(5) Uani 1 1 d . . . H24A H 0.5034 1.3131 0.4536 0.039 Uiso 1 1 calc R . . C25 C 0.4530(2) 1.38517(18) 0.53069(14) 0.0396(6) Uani 1 1 d . . . H25A H 0.4017 1.4320 0.5024 0.048 Uiso 1 1 calc R . . C26 C 0.4682(2) 1.3864(2) 0.60116(14) 0.0440(6) Uani 1 1 d . . . H26A H 0.4273 1.4348 0.6212 0.053 Uiso 1 1 calc R . . C27 C 0.5420(2) 1.3181(2) 0.64240(13) 0.0438(6) Uani 1 1 d . . . H27A H 0.5512 1.3195 0.6905 0.053 Uiso 1 1 calc R . . C28 C 0.60314(18) 1.2471(2) 0.61422(12) 0.0351(5) Uani 1 1 d . . . H28A H 0.6537 1.1998 0.6428 0.042 Uiso 1 1 calc R . . C29 C 0.75829(16) 1.07915(19) 0.56971(10) 0.0290(4) Uani 1 1 d . . . C30 C 0.85136(17) 1.1254(2) 0.60752(12) 0.0369(5) Uani 1 1 d . . . H30A H 0.8677 1.2007 0.6005 0.044 Uiso 1 1 calc R . . C31 C 0.92081(19) 1.0612(2) 0.65587(13) 0.0451(6) Uani 1 1 d . . . H31A H 0.9838 1.0935 0.6827 0.054 Uiso 1 1 calc R . . C32 C 0.8995(2) 0.9518(3) 0.66530(14) 0.0508(7) Uani 1 1 d . . . H32A H 0.9486 0.9083 0.6976 0.061 Uiso 1 1 calc R . . C33 C 0.8068(2) 0.9045(2) 0.62807(13) 0.0466(6) Uani 1 1 d . . . H33A H 0.7918 0.8288 0.6350 0.056 Uiso 1 1 calc R . . C34 C 0.73571(19) 0.9681(2) 0.58035(12) 0.0350(5) Uani 1 1 d . . . H34A H 0.6716 0.9361 0.5549 0.042 Uiso 1 1 calc R . . N41 N 0.2577(2) 1.0863(3) 0.2079(2) 0.0849(10) Uani 1 1 d . . . C42 C 0.1807(2) 1.1339(2) 0.19636(16) 0.0527(7) Uani 1 1 d . . . C43 C 0.0835(2) 1.1942(3) 0.18223(16) 0.0559(7) Uani 1 1 d . . . H43A H 0.0246 1.1418 0.1739 0.084 Uiso 1 1 calc R . . H43B H 0.0774 1.2408 0.1416 0.084 Uiso 1 1 calc R . . H43C H 0.0820 1.2414 0.2215 0.084 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 I1 0.03488(10) 0.03461(10) 0.02659(9) -0.00190(5) 0.01028(6) 0.00370(6) P1 0.0168(2) 0.0206(2) 0.0196(2) 0.00134(18) 0.00403(18) -0.00145(18) P19 0.0180(2) 0.0298(3) 0.0202(3) 0.00095(19) 0.00593(19) -0.00172(19) C1 0.0171(9) 0.0213(9) 0.0197(9) 0.0026(7) 0.0055(7) 0.0004(7) C2 0.0247(10) 0.0265(10) 0.0235(10) -0.0017(8) 0.0088(8) 0.0002(8) C3 0.0280(10) 0.0365(11) 0.0222(10) 0.0017(8) 0.0129(8) -0.0013(9) C4 0.0232(10) 0.0282(10) 0.0285(11) 0.0065(8) 0.0100(8) -0.0014(8) C5 0.0172(9) 0.0227(9) 0.0242(10) 0.0049(8) 0.0040(7) 0.0016(7) C6 0.0213(10) 0.0227(10) 0.0331(11) 0.0020(8) 0.0047(8) -0.0019(8) C7 0.0268(11) 0.0256(10) 0.0344(12) -0.0051(9) 0.0043(9) -0.0020(8) C8 0.0257(10) 0.0320(11) 0.0237(10) -0.0042(8) 0.0068(8) 0.0001(8) C9 0.0186(9) 0.0267(10) 0.0201(9) -0.0006(8) 0.0045(7) -0.0003(7) C10 0.0145(8) 0.0212(9) 0.0183(9) 0.0030(7) 0.0022(7) 0.0018(7) P9 0.0207(2) 0.0301(3) 0.0166(2) -0.00002(19) 0.00624(19) -0.00152(19) C11 0.0237(10) 0.0245(10) 0.0222(10) 0.0005(8) 0.0048(8) -0.0052(8) C12 0.0289(11) 0.0369(12) 0.0328(12) -0.0072(9) 0.0082(9) -0.0041(9) C13 0.0434(13) 0.0388(13) 0.0325(12) -0.0102(10) 0.0118(10) -0.0070(10) C14 0.0417(13) 0.0368(12) 0.0253(11) -0.0042(9) 0.0059(9) -0.0154(10) C15 0.0282(11) 0.0426(13) 0.0255(11) 0.0030(9) 0.0000(9) -0.0091(9) C16 0.0274(10) 0.0316(11) 0.0222(10) 0.0020(8) 0.0040(8) -0.0014(8) C17 0.0222(10) 0.0239(10) 0.0258(10) 0.0005(8) 0.0039(8) 0.0016(8) C18 0.0239(10) 0.0325(11) 0.0315(11) -0.0002(9) 0.0050(9) -0.0001(8) C19 0.0210(10) 0.0452(13) 0.0415(13) -0.0013(11) 0.0004(9) 0.0051(9) C20 0.0313(12) 0.0378(13) 0.0433(14) 0.0060(10) -0.0020(10) 0.0100(10) C21 0.0378(13) 0.0298(12) 0.0491(15) 0.0097(10) 0.0072(11) 0.0032(10) C22 0.0256(11) 0.0307(11) 0.0433(13) 0.0055(10) 0.0049(9) -0.0007(9) C23 0.0257(10) 0.0323(11) 0.0271(11) -0.0050(8) 0.0131(8) -0.0061(8) C24 0.0417(13) 0.0291(11) 0.0353(12) 0.0008(9) 0.0235(10) 0.0009(9) C25 0.0456(14) 0.0243(11) 0.0582(16) 0.0008(10) 0.0302(12) -0.0009(10) C26 0.0489(15) 0.0354(13) 0.0586(16) -0.0193(12) 0.0334(13) -0.0108(11) C27 0.0438(14) 0.0568(16) 0.0365(13) -0.0193(12) 0.0209(11) -0.0119(12) C28 0.0330(12) 0.0469(14) 0.0274(11) -0.0079(10) 0.0114(9) -0.0063(10) C29 0.0256(10) 0.0435(12) 0.0185(10) 0.0041(9) 0.0067(8) 0.0015(9) C30 0.0293(11) 0.0501(14) 0.0296(12) 0.0054(10) 0.0047(9) -0.0044(10) C31 0.0283(12) 0.0711(19) 0.0334(13) 0.0073(12) 0.0033(10) -0.0029(11) C32 0.0423(15) 0.0694(19) 0.0376(14) 0.0223(13) 0.0046(11) 0.0130(13) C33 0.0481(15) 0.0490(15) 0.0410(14) 0.0160(12) 0.0085(12) 0.0066(12) C34 0.0346(12) 0.0409(13) 0.0293(12) 0.0083(10) 0.0080(9) 0.0024(10) N41 0.0622(19) 0.074(2) 0.113(3) -0.0282(19) 0.0119(18) 0.0124(16) C42 0.0560(17) 0.0442(15) 0.0595(18) -0.0132(13) 0.0177(14) -0.0046(13) C43 0.0619(18) 0.0523(17) 0.0559(18) 0.0123(14) 0.0193(14) 0.0096(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C1 1.8062(19) . ? P1 C11 1.811(2) . ? P1 C17 1.812(2) . ? P1 P19 2.1172(7) . ? P19 P9 2.1178(7) . ? C1 C2 1.381(3) . ? C1 C10 1.436(3) . ? C2 C3 1.409(3) . ? C3 C4 1.361(3) . ? C4 C5 1.417(3) . ? C5 C6 1.416(3) . ? C5 C10 1.436(3) . ? C6 C7 1.364(3) . ? C7 C8 1.404(3) . ? C8 C9 1.386(3) . ? C9 C10 1.436(3) . ? C9 P9 1.8228(19) . ? P9 C23 1.809(2) . ? P9 C29 1.822(2) . ? C11 C16 1.391(3) . ? C11 C12 1.398(3) . ? C12 C13 1.390(3) . ? C13 C14 1.377(3) . ? C14 C15 1.377(3) . ? C15 C16 1.392(3) . ? C17 C18 1.380(3) . ? C17 C22 1.392(3) . ? C18 C19 1.397(3) . ? C19 C20 1.367(3) . ? C20 C21 1.385(3) . ? C21 C22 1.375(3) . ? C23 C28 1.395(3) . ? C23 C24 1.396(3) . ? C24 C25 1.391(3) . ? C25 C26 1.388(4) . ? C26 C27 1.378(4) . ? C27 C28 1.392(3) . ? C29 C30 1.384(3) . ? C29 C34 1.398(3) . ? C30 C31 1.390(3) . ? C31 C32 1.369(4) . ? C32 C33 1.381(4) . ? C33 C34 1.390(3) . ? N41 C42 1.135(4) . ? C42 C43 1.435(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C11 110.86(9) . . ? C1 P1 C17 106.93(9) . . ? C11 P1 C17 104.90(9) . . ? C1 P1 P19 114.33(6) . . ? C11 P1 P19 105.28(7) . . ? C17 P1 P19 114.16(7) . . ? P1 P19 P9 91.48(3) . . ? C2 C1 C10 120.65(17) . . ? C2 C1 P1 115.77(15) . . ? C10 C1 P1 123.57(14) . . ? C1 C2 C3 121.40(19) . . ? C4 C3 C2 119.76(18) . . ? C3 C4 C5 120.90(18) . . ? C6 C5 C4 118.95(18) . . ? C6 C5 C10 120.50(18) . . ? C4 C5 C10 120.55(18) . . ? C7 C6 C5 121.06(19) . . ? C6 C7 C8 119.59(19) . . ? C9 C8 C7 121.53(19) . . ? C8 C9 C10 120.52(18) . . ? C8 C9 P9 114.90(15) . . ? C10 C9 P9 124.58(14) . . ? C1 C10 C9 126.55(17) . . ? C1 C10 C5 116.72(16) . . ? C9 C10 C5 116.73(17) . . ? C23 P9 C29 108.45(10) . . ? C23 P9 C9 106.45(9) . . ? C29 P9 C9 107.07(9) . . ? C23 P9 P19 104.87(7) . . ? C29 P9 P19 115.31(8) . . ? C9 P9 P19 114.22(7) . . ? C16 C11 C12 119.56(19) . . ? C16 C11 P1 120.57(16) . . ? C12 C11 P1 119.80(16) . . ? C13 C12 C11 120.4(2) . . ? C14 C13 C12 119.5(2) . . ? C13 C14 C15 120.5(2) . . ? C14 C15 C16 120.8(2) . . ? C11 C16 C15 119.2(2) . . ? C18 C17 C22 119.53(19) . . ? C18 C17 P1 123.24(16) . . ? C22 C17 P1 117.20(15) . . ? C17 C18 C19 119.3(2) . . ? C20 C19 C18 120.8(2) . . ? C19 C20 C21 119.9(2) . . ? C22 C21 C20 119.9(2) . . ? C21 C22 C17 120.6(2) . . ? C28 C23 C24 120.2(2) . . ? C28 C23 P9 121.56(17) . . ? C24 C23 P9 118.27(16) . . ? C25 C24 C23 120.1(2) . . ? C26 C25 C24 119.4(2) . . ? C27 C26 C25 120.6(2) . . ? C26 C27 C28 120.7(2) . . ? C27 C28 C23 119.0(2) . . ? C30 C29 C34 119.5(2) . . ? C30 C29 P9 121.52(18) . . ? C34 C29 P9 118.89(17) . . ? C29 C30 C31 119.6(2) . . ? C32 C31 C30 120.8(2) . . ? C31 C32 C33 120.3(2) . . ? C32 C33 C34 119.6(3) . . ? C33 C34 C29 120.1(2) . . ? N41 C42 C43 179.6(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 P1 P19 P9 -49.67(7) . . . . ? C11 P1 P19 P9 -171.59(7) . . . . ? C17 P1 P19 P9 73.91(8) . . . . ? C11 P1 C1 C2 -26.55(18) . . . . ? C17 P1 C1 C2 87.26(16) . . . . ? P19 P1 C1 C2 -145.36(13) . . . . ? C11 P1 C1 C10 154.56(15) . . . . ? C17 P1 C1 C10 -91.63(16) . . . . ? P19 P1 C1 C10 35.75(17) . . . . ? C10 C1 C2 C3 1.2(3) . . . . ? P1 C1 C2 C3 -177.68(16) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 -1.0(3) . . . . ? C3 C4 C5 C6 -179.56(19) . . . . ? C3 C4 C5 C10 0.3(3) . . . . ? C4 C5 C6 C7 178.30(19) . . . . ? C10 C5 C6 C7 -1.6(3) . . . . ? C5 C6 C7 C8 -0.6(3) . . . . ? C6 C7 C8 C9 2.4(3) . . . . ? C7 C8 C9 C10 -2.0(3) . . . . ? C7 C8 C9 P9 177.87(16) . . . . ? C2 C1 C10 C9 177.09(18) . . . . ? P1 C1 C10 C9 -4.1(3) . . . . ? C2 C1 C10 C5 -1.8(3) . . . . ? P1 C1 C10 C5 177.00(13) . . . . ? C8 C9 C10 C1 -179.11(18) . . . . ? P9 C9 C10 C1 1.1(3) . . . . ? C8 C9 C10 C5 -0.2(3) . . . . ? P9 C9 C10 C5 180.00(14) . . . . ? C6 C5 C10 C1 -179.06(17) . . . . ? C4 C5 C10 C1 1.1(3) . . . . ? C6 C5 C10 C9 1.9(3) . . . . ? C4 C5 C10 C9 -177.95(17) . . . . ? C8 C9 P9 C23 35.01(17) . . . . ? C10 C9 P9 C23 -145.16(16) . . . . ? C8 C9 P9 C29 -80.83(17) . . . . ? C10 C9 P9 C29 99.00(17) . . . . ? C8 C9 P9 P19 150.23(13) . . . . ? C10 C9 P9 P19 -29.94(18) . . . . ? P1 P19 P9 C23 163.01(7) . . . . ? P1 P19 P9 C29 -77.80(8) . . . . ? P1 P19 P9 C9 46.87(7) . . . . ? C1 P1 C11 C16 -100.84(17) . . . . ? C17 P1 C11 C16 144.07(17) . . . . ? P19 P1 C11 C16 23.30(18) . . . . ? C1 P1 C11 C12 82.31(18) . . . . ? C17 P1 C11 C12 -32.77(19) . . . . ? P19 P1 C11 C12 -153.55(16) . . . . ? C16 C11 C12 C13 -1.2(3) . . . . ? P1 C11 C12 C13 175.66(18) . . . . ? C11 C12 C13 C14 -1.0(4) . . . . ? C12 C13 C14 C15 2.2(4) . . . . ? C13 C14 C15 C16 -1.0(3) . . . . ? C12 C11 C16 C15 2.3(3) . . . . ? P1 C11 C16 C15 -174.51(16) . . . . ? C14 C15 C16 C11 -1.3(3) . . . . ? C1 P1 C17 C18 2.7(2) . . . . ? C11 P1 C17 C18 120.48(19) . . . . ? P19 P1 C17 C18 -124.79(17) . . . . ? C1 P1 C17 C22 -179.51(17) . . . . ? C11 P1 C17 C22 -61.72(19) . . . . ? P19 P1 C17 C22 53.00(19) . . . . ? C22 C17 C18 C19 -2.7(3) . . . . ? P1 C17 C18 C19 175.05(17) . . . . ? C17 C18 C19 C20 0.1(4) . . . . ? C18 C19 C20 C21 2.6(4) . . . . ? C19 C20 C21 C22 -2.7(4) . . . . ? C20 C21 C22 C17 0.2(4) . . . . ? C18 C17 C22 C21 2.6(3) . . . . ? P1 C17 C22 C21 -175.31(19) . . . . ? C29 P9 C23 C28 -0.4(2) . . . . ? C9 P9 C23 C28 -115.25(18) . . . . ? P19 P9 C23 C28 123.35(17) . . . . ? C29 P9 C23 C24 179.76(16) . . . . ? C9 P9 C23 C24 64.86(18) . . . . ? P19 P9 C23 C24 -56.53(17) . . . . ? C28 C23 C24 C25 0.9(3) . . . . ? P9 C23 C24 C25 -179.17(17) . . . . ? C23 C24 C25 C26 -0.2(3) . . . . ? C24 C25 C26 C27 -0.4(4) . . . . ? C25 C26 C27 C28 0.4(4) . . . . ? C26 C27 C28 C23 0.3(4) . . . . ? C24 C23 C28 C27 -1.0(3) . . . . ? P9 C23 C28 C27 179.14(17) . . . . ? C23 P9 C29 C30 -80.8(2) . . . . ? C9 P9 C29 C30 33.7(2) . . . . ? P19 P9 C29 C30 161.98(16) . . . . ? C23 P9 C29 C34 102.14(18) . . . . ? C9 P9 C29 C34 -143.36(17) . . . . ? P19 P9 C29 C34 -15.05(19) . . . . ? C34 C29 C30 C31 -0.4(3) . . . . ? P9 C29 C30 C31 -177.44(18) . . . . ? C29 C30 C31 C32 1.7(4) . . . . ? C30 C31 C32 C33 -1.8(4) . . . . ? C31 C32 C33 C34 0.7(4) . . . . ? C32 C33 C34 C29 0.6(4) . . . . ? C30 C29 C34 C33 -0.7(3) . . . . ? P9 C29 C34 C33 176.42(19) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.762 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.055 # Attachment '5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 291571' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H24 N3 P2.I' _chemical_formula_sum 'C16 H24 I N3 P2' _chemical_formula_weight 447.22 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.133(4) _cell_length_b 8.0121(19) _cell_length_c 15.587(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.942(6) _cell_angle_gamma 90.00 _cell_volume 1882.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 6801 _cell_measurement_theta_min 1.7989 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.1500 _exptl_crystal_size_min 0.1000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 1.871 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7524 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11025 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3373 _reflns_number_gt 3041 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0133P)^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 3373 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0532 _refine_ls_wR_factor_gt 0.0508 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.394232(12) 0.22627(2) -0.358425(11) 0.02846(8) Uani 1 1 d . . . P1 P 0.24998(4) 0.25272(7) 0.00181(4) 0.01534(15) Uani 1 1 d . . . P9 P 0.28450(4) 0.48412(8) 0.07934(4) 0.01866(15) Uani 1 1 d . . . N1 N 0.26269(13) 0.2904(2) -0.09945(12) 0.0190(5) Uani 1 1 d . . . N2 N 0.15155(12) 0.1757(3) 0.00719(12) 0.0192(4) Uani 1 1 d . . . N3 N 0.21114(13) 0.4865(2) 0.15396(12) 0.0230(5) Uani 1 1 d . . . C1 C 0.33189(15) 0.1135(3) 0.05114(14) 0.0180(5) Uani 1 1 d . . . C2 C 0.34576(16) -0.0499(3) 0.02978(15) 0.0208(6) Uani 1 1 d . . . H2A H 0.3046 -0.1057 -0.0098 0.025 Uiso 1 1 calc R . . C3 C 0.42166(17) -0.1351(3) 0.06680(16) 0.0258(6) Uani 1 1 d . . . H3A H 0.4315 -0.2479 0.0516 0.031 Uiso 1 1 calc R . . C4 C 0.48093(16) -0.0558(3) 0.12438(16) 0.0239(6) Uani 1 1 d . . . H4A H 0.5311 -0.1155 0.1491 0.029 Uiso 1 1 calc R . . C5 C 0.46935(15) 0.1118(3) 0.14778(15) 0.0204(5) Uani 1 1 d . . . C6 C 0.52905(16) 0.1985(3) 0.20807(16) 0.0248(6) Uani 1 1 d . . . H6A H 0.5792 0.1419 0.2350 0.030 Uiso 1 1 calc R . . C7 C 0.51484(16) 0.3614(3) 0.22730(16) 0.0256(6) Uani 1 1 d . . . H7A H 0.5559 0.4174 0.2669 0.031 Uiso 1 1 calc R . . C8 C 0.44034(16) 0.4489(3) 0.18951(15) 0.0222(6) Uani 1 1 d . . . H8A H 0.4320 0.5627 0.2039 0.027 Uiso 1 1 calc R . . C9 C 0.37964(15) 0.3705(3) 0.13192(14) 0.0180(5) Uani 1 1 d . . . C10 C 0.39332(15) 0.1998(3) 0.11026(15) 0.0164(5) Uani 1 1 d . . . C11 C 0.32197(17) 0.4234(3) -0.12500(16) 0.0279(6) Uani 1 1 d . . . H11A H 0.3838 0.3878 -0.1133 0.042 Uiso 1 1 calc R . . H11B H 0.3119 0.5249 -0.0921 0.042 Uiso 1 1 calc R . . H11C H 0.3098 0.4462 -0.1867 0.042 Uiso 1 1 calc R . . C12 C 0.24879(17) 0.1542(3) -0.16226(15) 0.0283(6) Uani 1 1 d . . . H12A H 0.2283 0.2004 -0.2187 0.042 Uiso 1 1 calc R . . H12B H 0.2041 0.0770 -0.1435 0.042 Uiso 1 1 calc R . . H12C H 0.3047 0.0943 -0.1665 0.042 Uiso 1 1 calc R . . C13 C 0.07461(17) 0.2559(3) -0.03992(18) 0.0267(6) Uani 1 1 d . . . H13A H 0.0450 0.1758 -0.0803 0.040 Uiso 1 1 calc R . . H13B H 0.0945 0.3523 -0.0718 0.040 Uiso 1 1 calc R . . H13C H 0.0330 0.2930 0.0010 0.040 Uiso 1 1 calc R . . C14 C 0.12891(17) 0.0380(3) 0.06341(16) 0.0250(6) Uani 1 1 d . . . H14A H 0.0839 0.0756 0.1007 0.037 Uiso 1 1 calc R . . H14B H 0.1822 0.0024 0.0989 0.037 Uiso 1 1 calc R . . H14C H 0.1055 -0.0559 0.0281 0.037 Uiso 1 1 calc R . . C15 C 0.13360(17) 0.5947(3) 0.13689(17) 0.0322(7) Uani 1 1 d . . . H15A H 0.0815 0.5263 0.1191 0.048 Uiso 1 1 calc R . . H15B H 0.1443 0.6735 0.0908 0.048 Uiso 1 1 calc R . . H15C H 0.1231 0.6566 0.1893 0.048 Uiso 1 1 calc R . . C16 C 0.19738(18) 0.3539(3) 0.21633(16) 0.0306(6) Uani 1 1 d . . . H16A H 0.1896 0.4037 0.2726 0.046 Uiso 1 1 calc R . . H16B H 0.2491 0.2798 0.2213 0.046 Uiso 1 1 calc R . . H16C H 0.1443 0.2897 0.1968 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.03680(13) 0.02200(12) 0.02838(13) -0.00028(7) 0.01319(9) 0.00053(7) P1 0.0152(3) 0.0141(3) 0.0166(3) 0.0014(2) 0.0011(3) -0.0024(2) P9 0.0210(3) 0.0125(3) 0.0224(4) 0.0003(3) 0.0016(3) -0.0012(3) N1 0.0215(11) 0.0182(11) 0.0180(11) 0.0021(8) 0.0049(9) -0.0036(9) N2 0.0175(10) 0.0189(11) 0.0212(11) 0.0028(9) 0.0025(9) -0.0036(9) N3 0.0249(11) 0.0202(12) 0.0243(11) -0.0005(9) 0.0050(10) 0.0048(9) C1 0.0191(12) 0.0169(13) 0.0181(12) 0.0034(10) 0.0025(10) -0.0010(10) C2 0.0239(13) 0.0168(13) 0.0218(13) 0.0004(10) 0.0027(11) -0.0045(11) C3 0.0298(14) 0.0144(14) 0.0345(15) 0.0042(11) 0.0104(12) 0.0012(11) C4 0.0197(12) 0.0205(14) 0.0318(15) 0.0084(11) 0.0049(12) 0.0042(11) C5 0.0160(12) 0.0232(14) 0.0222(13) 0.0063(11) 0.0025(11) -0.0018(10) C6 0.0150(12) 0.0308(15) 0.0283(15) 0.0043(12) -0.0002(11) -0.0018(11) C7 0.0217(13) 0.0298(16) 0.0248(14) 0.0005(12) -0.0016(11) -0.0088(11) C8 0.0273(13) 0.0188(13) 0.0209(13) -0.0017(11) 0.0044(11) -0.0053(11) C9 0.0162(11) 0.0180(13) 0.0199(13) 0.0034(10) 0.0032(11) -0.0017(10) C10 0.0182(12) 0.0151(12) 0.0167(12) 0.0017(10) 0.0062(10) -0.0028(10) C11 0.0328(15) 0.0225(15) 0.0301(15) 0.0052(11) 0.0119(12) -0.0040(12) C12 0.0295(14) 0.0339(17) 0.0215(14) -0.0068(12) 0.0034(12) -0.0052(12) C13 0.0179(13) 0.0327(16) 0.0290(16) 0.0062(11) -0.0006(12) -0.0003(11) C14 0.0278(14) 0.0216(14) 0.0265(14) 0.0038(11) 0.0075(12) -0.0079(11) C15 0.0300(15) 0.0287(16) 0.0379(16) -0.0032(13) 0.0023(13) 0.0108(13) C16 0.0336(15) 0.0336(17) 0.0261(14) 0.0037(12) 0.0110(12) 0.0014(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N2 1.621(2) . ? P1 N1 1.635(2) . ? P1 C1 1.791(2) . ? P1 P9 2.2498(9) . ? P9 N3 1.676(2) . ? P9 C9 1.836(2) . ? N1 C12 1.469(3) . ? N1 C11 1.470(3) . ? N2 C14 1.468(3) . ? N2 C13 1.470(3) . ? N3 C15 1.464(3) . ? N3 C16 1.467(3) . ? C1 C2 1.371(3) . ? C1 C10 1.430(3) . ? C2 C3 1.416(3) . ? C2 H2A 0.9500 . ? C3 C4 1.369(3) . ? C3 H3A 0.9500 . ? C4 C5 1.407(3) . ? C4 H4A 0.9500 . ? C5 C6 1.427(3) . ? C5 C10 1.431(3) . ? C6 C7 1.361(4) . ? C6 H6A 0.9500 . ? C7 C8 1.413(3) . ? C7 H7A 0.9500 . ? C8 C9 1.379(3) . ? C8 H8A 0.9500 . ? C9 C10 1.428(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 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 N2 P1 N1 107.78(10) . . ? N2 P1 C1 110.23(11) . . ? N1 P1 C1 113.26(11) . . ? N2 P1 P9 117.25(8) . . ? N1 P1 P9 108.97(8) . . ? C1 P1 P9 99.35(8) . . ? N3 P9 C9 103.70(10) . . ? N3 P9 P1 104.20(8) . . ? C9 P9 P1 88.18(8) . . ? C12 N1 C11 114.4(2) . . ? C12 N1 P1 118.95(17) . . ? C11 N1 P1 121.40(16) . . ? C14 N2 C13 114.27(19) . . ? C14 N2 P1 125.44(16) . . ? C13 N2 P1 119.98(16) . . ? C15 N3 C16 113.1(2) . . ? C15 N3 P9 116.69(17) . . ? C16 N3 P9 126.29(17) . . ? C2 C1 C10 120.9(2) . . ? C2 C1 P1 127.23(17) . . ? C10 C1 P1 111.29(17) . . ? C1 C2 C3 119.8(2) . . ? C1 C2 H2A 120.1 . . ? C3 C2 H2A 120.1 . . ? C4 C3 C2 120.4(2) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C5 121.6(2) . . ? C3 C4 H4A 119.2 . . ? C5 C4 H4A 119.2 . . ? C4 C5 C6 123.3(2) . . ? C4 C5 C10 118.6(2) . . ? C6 C5 C10 118.1(2) . . ? C7 C6 C5 120.6(2) . . ? C7 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C6 C7 C8 121.3(2) . . ? C6 C7 H7A 119.3 . . ? C8 C7 H7A 119.3 . . ? C9 C8 C7 120.6(2) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C8 C9 C10 119.2(2) . . ? C8 C9 P9 121.19(19) . . ? C10 C9 P9 119.56(16) . . ? C9 C10 C1 121.1(2) . . ? C9 C10 C5 120.2(2) . . ? C1 C10 C5 118.7(2) . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C16 H16A 109.5 . . ? N3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 N2 P1 P9 N3 19.91(11) . . . . ? N1 P1 P9 N3 142.62(10) . . . . ? C1 P1 P9 N3 -98.71(11) . . . . ? N2 P1 P9 C9 123.59(11) . . . . ? N1 P1 P9 C9 -113.71(11) . . . . ? C1 P1 P9 C9 4.96(11) . . . . ? N2 P1 N1 C12 -55.2(2) . . . . ? C1 P1 N1 C12 67.0(2) . . . . ? P9 P1 N1 C12 176.60(16) . . . . ? N2 P1 N1 C11 151.74(19) . . . . ? C1 P1 N1 C11 -86.0(2) . . . . ? P9 P1 N1 C11 23.5(2) . . . . ? N1 P1 N2 C14 139.7(2) . . . . ? C1 P1 N2 C14 15.6(2) . . . . ? P9 P1 N2 C14 -97.0(2) . . . . ? N1 P1 N2 C13 -47.1(2) . . . . ? C1 P1 N2 C13 -171.15(18) . . . . ? P9 P1 N2 C13 76.23(19) . . . . ? C9 P9 N3 C15 169.47(18) . . . . ? P1 P9 N3 C15 -98.93(17) . . . . ? C9 P9 N3 C16 -34.6(2) . . . . ? P1 P9 N3 C16 57.0(2) . . . . ? N2 P1 C1 C2 57.7(3) . . . . ? N1 P1 C1 C2 -63.2(3) . . . . ? P9 P1 C1 C2 -178.6(2) . . . . ? N2 P1 C1 C10 -131.09(17) . . . . ? N1 P1 C1 C10 108.07(18) . . . . ? P9 P1 C1 C10 -7.36(18) . . . . ? C10 C1 C2 C3 0.2(4) . . . . ? P1 C1 C2 C3 170.7(2) . . . . ? C1 C2 C3 C4 0.6(4) . . . . ? C2 C3 C4 C5 -0.8(4) . . . . ? C3 C4 C5 C6 179.4(2) . . . . ? C3 C4 C5 C10 0.3(4) . . . . ? C4 C5 C6 C7 179.2(3) . . . . ? C10 C5 C6 C7 -1.7(4) . . . . ? C5 C6 C7 C8 1.0(4) . . . . ? C6 C7 C8 C9 0.1(4) . . . . ? C7 C8 C9 C10 -0.5(4) . . . . ? C7 C8 C9 P9 -177.87(19) . . . . ? N3 P9 C9 C8 -80.6(2) . . . . ? P1 P9 C9 C8 175.2(2) . . . . ? N3 P9 C9 C10 102.1(2) . . . . ? P1 P9 C9 C10 -2.11(19) . . . . ? C8 C9 C10 C1 179.7(2) . . . . ? P9 C9 C10 C1 -2.9(3) . . . . ? C8 C9 C10 C5 -0.2(3) . . . . ? P9 C9 C10 C5 177.18(18) . . . . ? C2 C1 C10 C9 179.3(2) . . . . ? P1 C1 C10 C9 7.4(3) . . . . ? C2 C1 C10 C5 -0.8(4) . . . . ? P1 C1 C10 C5 -172.64(18) . . . . ? C4 C5 C10 C9 -179.5(2) . . . . ? C6 C5 C10 C9 1.3(3) . . . . ? C4 C5 C10 C1 0.5(3) . . . . ? C6 C5 C10 C1 -178.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.540 _refine_diff_density_min -0.688 _refine_diff_density_rms 0.072 # Attachment '6.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 291572' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H36 I2 N4 P4' _chemical_formula_sum 'C28 H36 I2 N4 P4' _chemical_formula_weight 806.29 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.376(4) _cell_length_b 18.552(4) _cell_length_c 13.197(3) _cell_angle_alpha 90.00 _cell_angle_beta 117.087(6) _cell_angle_gamma 90.00 _cell_volume 3133.4(13) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 5388 _cell_measurement_theta_min 3.0402 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Chunk _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.1500 _exptl_crystal_size_mid 0.1500 _exptl_crystal_size_min 0.1500 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1592 _exptl_absorpt_coefficient_mu 2.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6879 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9262 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0856 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2799 _reflns_number_gt 2221 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0164P)^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 2799 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0623 _refine_ls_wR_factor_gt 0.0589 _refine_ls_goodness_of_fit_ref 0.786 _refine_ls_restrained_S_all 0.786 _refine_ls_shift/su_max 0.037 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 1.0000 0.227343(18) 0.2500 0.02083(12) Uani 1 2 d S . . I2 I 0.5000 -0.10165(2) -0.2500 0.03177(13) Uani 1 2 d S . . P1 P 0.96014(7) 0.04675(5) 0.15283(7) 0.0125(2) Uani 1 1 d . . . C1 C 0.9333(3) -0.04990(19) 0.1246(2) 0.0158(8) Uani 1 1 d . . . C2 C 1.0017(3) -0.0966(2) 0.1123(2) 0.0234(10) Uani 1 1 d . . . H2A H 1.0629 -0.0783 0.1110 0.028 Uiso 1 1 calc R . . C3 C 0.9818(4) -0.1715(2) 0.1015(3) 0.0290(11) Uani 1 1 d . . . H3A H 1.0297 -0.2030 0.0926 0.035 Uiso 1 1 calc R . . C4 C 0.8951(4) -0.1994(2) 0.1037(3) 0.0328(12) Uani 1 1 d . . . H4A H 0.8851 -0.2501 0.0996 0.039 Uiso 1 1 calc R . . C5 C 0.8201(3) -0.1543(2) 0.1120(2) 0.0259(10) Uani 1 1 d . . . C6 C 0.7293(4) -0.1787(2) 0.1172(3) 0.0322(12) Uani 1 1 d . . . H6A H 0.7151 -0.2290 0.1115 0.039 Uiso 1 1 calc R . . C7 C 0.6606(3) -0.1327(2) 0.1301(3) 0.0340(11) Uani 1 1 d . . . H7A H 0.6009 -0.1513 0.1342 0.041 Uiso 1 1 calc R . . C8 C 0.6790(3) -0.0573(2) 0.1371(3) 0.0235(9) Uani 1 1 d . . . H8A H 0.6317 -0.0251 0.1456 0.028 Uiso 1 1 calc R . . C9 C 0.7662(3) -0.03156(19) 0.1316(2) 0.0171(8) Uani 1 1 d . . . C10 C 0.8391(3) -0.07815(19) 0.1220(2) 0.0185(9) Uani 1 1 d . . . P9 P 0.79678(7) 0.06137(5) 0.12564(7) 0.0124(2) Uani 1 1 d . . . N1 N 0.7364(2) 0.08909(15) -0.0063(2) 0.0162(7) Uani 1 1 d . . . C11 C 0.7757(3) 0.1471(2) -0.0502(3) 0.0240(9) Uani 1 1 d . . . H11A H 0.7748 0.1318 -0.1217 0.036 Uiso 1 1 calc R . . H11B H 0.8474 0.1588 0.0055 0.036 Uiso 1 1 calc R . . H11C H 0.7313 0.1897 -0.0640 0.036 Uiso 1 1 calc R . . C12 C 0.6244(3) 0.0743(2) -0.0763(3) 0.0370(12) Uani 1 1 d . . . H12A H 0.5834 0.1150 -0.0711 0.055 Uiso 1 1 calc R . . H12B H 0.6053 0.0305 -0.0487 0.055 Uiso 1 1 calc R . . H12C H 0.6100 0.0675 -0.1558 0.055 Uiso 1 1 calc R . . N2 N 0.7595(2) 0.10687(15) 0.2065(2) 0.0159(7) Uani 1 1 d . . . C13 C 0.7170(3) 0.18060(19) 0.1763(3) 0.0230(9) Uani 1 1 d . . . H13A H 0.6645 0.1885 0.2032 0.034 Uiso 1 1 calc R . . H13B H 0.6846 0.1866 0.0935 0.034 Uiso 1 1 calc R . . H13C H 0.7737 0.2157 0.2122 0.034 Uiso 1 1 calc R . . C14 C 0.7932(3) 0.0870(2) 0.3256(3) 0.0242(10) Uani 1 1 d . . . H14A H 0.8476 0.1204 0.3754 0.036 Uiso 1 1 calc R . . H14B H 0.8210 0.0378 0.3388 0.036 Uiso 1 1 calc R . . H14C H 0.7334 0.0895 0.3422 0.036 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 I1 0.0133(2) 0.0127(2) 0.0324(2) 0.000 0.00684(15) 0.000 I2 0.0165(2) 0.0208(2) 0.0587(3) 0.000 0.01777(19) 0.000 P1 0.0134(5) 0.0119(5) 0.0114(4) 0.0003(4) 0.0051(4) 0.0020(4) C1 0.024(2) 0.013(2) 0.0046(15) -0.0013(13) 0.0019(15) 0.0011(18) C2 0.034(3) 0.022(2) 0.0087(17) 0.0000(15) 0.0051(17) 0.009(2) C3 0.043(3) 0.021(2) 0.0116(18) -0.0015(15) 0.0022(18) 0.016(2) C4 0.059(3) 0.006(2) 0.0136(18) -0.0017(15) -0.0009(19) 0.006(2) C5 0.038(3) 0.018(2) 0.0062(16) 0.0042(15) -0.0034(16) -0.007(2) C6 0.049(3) 0.017(2) 0.0111(18) 0.0016(16) -0.0037(18) -0.018(2) C7 0.033(3) 0.038(3) 0.0181(19) 0.0066(18) 0.0003(18) -0.023(2) C8 0.019(2) 0.025(2) 0.0195(19) 0.0001(16) 0.0033(16) -0.0070(19) C9 0.017(2) 0.017(2) 0.0118(16) 0.0022(15) 0.0016(15) -0.0046(18) C10 0.025(2) 0.014(2) 0.0069(16) 0.0021(14) -0.0016(15) -0.0020(18) P9 0.0120(5) 0.0117(5) 0.0117(4) -0.0003(4) 0.0038(4) -0.0022(4) N1 0.0142(18) 0.0126(17) 0.0139(14) 0.0003(12) -0.0005(13) -0.0049(13) C11 0.021(2) 0.031(2) 0.0186(18) 0.0089(17) 0.0078(16) 0.0079(19) C12 0.022(3) 0.037(3) 0.029(2) 0.0116(19) -0.0081(18) -0.009(2) N2 0.0124(17) 0.0192(18) 0.0166(14) -0.0012(13) 0.0070(12) 0.0001(14) C13 0.025(2) 0.017(2) 0.038(2) -0.0090(17) 0.0234(19) -0.0022(18) C14 0.015(2) 0.040(3) 0.0183(18) -0.0016(17) 0.0080(16) 0.0027(19) _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 C1 1.836(4) . ? P1 P9 2.2249(14) . ? P1 P1 2.2835(17) 2_755 ? C1 C2 1.374(5) . ? C1 C10 1.438(5) . ? C2 C3 1.413(5) . ? C2 H2A 0.9500 . ? C3 C4 1.362(6) . ? C3 H3A 0.9500 . ? C4 C5 1.408(6) . ? C4 H4A 0.9500 . ? C5 C6 1.413(6) . ? C5 C10 1.433(5) . ? C6 C7 1.373(6) . ? C6 H6A 0.9500 . ? C7 C8 1.418(5) . ? C7 H7A 0.9500 . ? C8 C9 1.373(5) . ? C8 H8A 0.9500 . ? C9 C10 1.408(5) . ? C9 P9 1.790(4) . ? P9 N2 1.630(3) . ? P9 N1 1.635(3) . ? N1 C11 1.453(4) . ? N1 C12 1.472(5) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? N2 C14 1.466(4) . ? N2 C13 1.477(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 C1 P1 P9 88.71(13) . . ? C1 P1 P1 100.32(9) . 2_755 ? P9 P1 P1 97.71(6) . 2_755 ? C2 C1 C10 119.0(3) . . ? C2 C1 P1 122.9(3) . . ? C10 C1 P1 118.0(3) . . ? C1 C2 C3 120.6(4) . . ? C1 C2 H2A 119.7 . . ? C3 C2 H2A 119.7 . . ? C4 C3 C2 121.1(4) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C3 C4 C5 121.1(4) . . ? C3 C4 H4A 119.4 . . ? C5 C4 H4A 119.4 . . ? C4 C5 C6 124.8(4) . . ? C4 C5 C10 118.1(4) . . ? C6 C5 C10 117.0(4) . . ? C7 C6 C5 122.6(4) . . ? C7 C6 H6A 118.7 . . ? C5 C6 H6A 118.7 . . ? C6 C7 C8 119.9(4) . . ? C6 C7 H7A 120.1 . . ? C8 C7 H7A 120.1 . . ? C9 C8 C7 119.1(4) . . ? C9 C8 H8A 120.4 . . ? C7 C8 H8A 120.4 . . ? C8 C9 C10 121.7(4) . . ? C8 C9 P9 125.9(3) . . ? C10 C9 P9 112.3(3) . . ? C9 C10 C5 119.6(4) . . ? C9 C10 C1 120.4(3) . . ? C5 C10 C1 120.0(4) . . ? N2 P9 N1 111.11(15) . . ? N2 P9 C9 108.01(16) . . ? N1 P9 C9 109.15(14) . . ? N2 P9 P1 126.50(11) . . ? N1 P9 P1 102.71(11) . . ? C9 P9 P1 97.94(13) . . ? C11 N1 C12 113.6(3) . . ? C11 N1 P9 122.9(2) . . ? C12 N1 P9 120.6(2) . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 N2 C13 114.6(3) . . ? C14 N2 P9 121.7(2) . . ? C13 N2 P9 121.5(2) . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 P9 P1 C1 C2 171.3(2) . . . . ? P1 P1 C1 C2 -91.1(3) 2_755 . . . ? P9 P1 C1 C10 -12.3(2) . . . . ? P1 P1 C1 C10 85.3(2) 2_755 . . . ? C10 C1 C2 C3 -2.4(4) . . . . ? P1 C1 C2 C3 173.9(2) . . . . ? C1 C2 C3 C4 -0.4(5) . . . . ? C2 C3 C4 C5 2.7(5) . . . . ? C3 C4 C5 C6 -178.6(3) . . . . ? C3 C4 C5 C10 -2.0(5) . . . . ? C4 C5 C6 C7 177.2(3) . . . . ? C10 C5 C6 C7 0.6(5) . . . . ? C5 C6 C7 C8 0.9(5) . . . . ? C6 C7 C8 C9 -0.4(5) . . . . ? C7 C8 C9 C10 -1.6(5) . . . . ? C7 C8 C9 P9 173.8(2) . . . . ? C8 C9 C10 C5 3.1(5) . . . . ? P9 C9 C10 C5 -172.9(2) . . . . ? C8 C9 C10 C1 -175.5(3) . . . . ? P9 C9 C10 C1 8.5(4) . . . . ? C4 C5 C10 C9 -179.3(3) . . . . ? C6 C5 C10 C9 -2.5(4) . . . . ? C4 C5 C10 C1 -0.8(4) . . . . ? C6 C5 C10 C1 176.1(3) . . . . ? C2 C1 C10 C9 -178.5(3) . . . . ? P1 C1 C10 C9 5.0(4) . . . . ? C2 C1 C10 C5 3.0(4) . . . . ? P1 C1 C10 C5 -173.6(2) . . . . ? C8 C9 P9 N2 37.0(3) . . . . ? C10 C9 P9 N2 -147.2(2) . . . . ? C8 C9 P9 N1 -83.9(3) . . . . ? C10 C9 P9 N1 91.9(3) . . . . ? C8 C9 P9 P1 169.6(3) . . . . ? C10 C9 P9 P1 -14.6(2) . . . . ? C1 P1 P9 N2 133.22(16) . . . . ? P1 P1 P9 N2 32.97(14) 2_755 . . . ? C1 P1 P9 N1 -98.00(14) . . . . ? P1 P1 P9 N1 161.76(10) 2_755 . . . ? C1 P1 P9 C9 13.77(14) . . . . ? P1 P1 P9 C9 -86.47(10) 2_755 . . . ? N2 P9 N1 C11 88.9(3) . . . . ? C9 P9 N1 C11 -152.1(3) . . . . ? P1 P9 N1 C11 -48.9(3) . . . . ? N2 P9 N1 C12 -70.6(3) . . . . ? C9 P9 N1 C12 48.4(3) . . . . ? P1 P9 N1 C12 151.6(3) . . . . ? N1 P9 N2 C14 172.9(3) . . . . ? C9 P9 N2 C14 53.2(3) . . . . ? P1 P9 N2 C14 -61.7(3) . . . . ? N1 P9 N2 C13 -25.1(3) . . . . ? C9 P9 N2 C13 -144.8(3) . . . . ? P1 P9 N2 C13 100.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.854 _refine_diff_density_min -0.675 _refine_diff_density_rms 0.135 # Attachment '7.CIF' data_7 _database_code_depnum_ccdc_archive 'CCDC 291573' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 I2 N2 P2' _chemical_formula_sum 'C14 H18 I2 N2 P2' _chemical_formula_weight 530.04 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.532(3) _cell_length_b 9.024(2) _cell_length_c 13.837(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.131(9) _cell_angle_gamma 90.00 _cell_volume 916.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3109 _cell_measurement_theta_min 2.2578 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Platelet _exptl_crystal_colour yellow _exptl_crystal_size_max 0.1800 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.0600 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.922 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 3.601 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5980 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5726 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2953 _reflns_number_gt 2445 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0305P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(3) _refine_ls_number_reflns 2953 _refine_ls_number_parameters 186 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0650 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I -0.25094(7) -0.88983(5) -0.29642(3) 0.06460(16) Uani 1 1 d . . . I2 I 0.63142(8) -0.60305(6) 0.30481(4) 0.07763(19) Uani 1 1 d . . . P1 P 0.0135(3) -0.72551(18) -0.30091(13) 0.0501(4) Uani 1 1 d . . . C1 C 0.1262(9) -0.6920(8) -0.1723(5) 0.0518(17) Uani 1 1 d . . . C2 C 0.2435(10) -0.7920(10) -0.1154(6) 0.075(2) Uani 1 1 d . . . H2A H 0.2582 -0.8882 -0.1402 0.091 Uiso 1 1 calc R . . C3 C 0.3426(11) -0.7499(15) -0.0189(7) 0.087(3) Uani 1 1 d . . . H3A H 0.4187 -0.8210 0.0210 0.105 Uiso 1 1 calc R . . C4 C 0.3321(11) -0.6139(15) 0.0173(6) 0.088(3) Uani 1 1 d . . . H4A H 0.4039 -0.5892 0.0810 0.105 Uiso 1 1 calc R . . C5 C 0.2166(10) -0.5074(11) -0.0375(5) 0.067(2) Uani 1 1 d . . . C6 C 0.2010(12) -0.3607(13) -0.0037(6) 0.084(3) Uani 1 1 d . . . H6A H 0.2708 -0.3318 0.0596 0.101 Uiso 1 1 calc R . . C7 C 0.0885(14) -0.2611(12) -0.0598(7) 0.086(3) Uani 1 1 d . . . H7A H 0.0832 -0.1627 -0.0362 0.103 Uiso 1 1 calc R . . C8 C -0.0214(11) -0.3013(9) -0.1535(6) 0.067(2) Uani 1 1 d . . . H8A H -0.1013 -0.2315 -0.1925 0.080 Uiso 1 1 calc R . . C9 C -0.0098(9) -0.4434(7) -0.1866(5) 0.0499(16) Uani 1 1 d . . . C10 C 0.1101(9) -0.5489(8) -0.1327(4) 0.0491(16) Uani 1 1 d . . . P9 P -0.1351(2) -0.51195(17) -0.30345(11) 0.0382(4) Uani 1 1 d . . . N1 N -0.3495(7) -0.5080(6) -0.3027(4) 0.0460(12) Uani 1 1 d . . . C11 C -0.4192(11) -0.5186(10) -0.2125(6) 0.072(2) Uani 1 1 d . . . H11A H -0.5021 -0.4356 -0.2101 0.109 Uiso 1 1 calc R . . H11B H -0.3171 -0.5149 -0.1542 0.109 Uiso 1 1 calc R . . H11C H -0.4850 -0.6123 -0.2127 0.109 Uiso 1 1 calc R . . C12 C -0.4867(11) -0.5341(11) -0.3942(7) 0.085(3) Uani 1 1 d . . . H12A H -0.5535 -0.6254 -0.3877 0.128 Uiso 1 1 calc R . . H12B H -0.4268 -0.5439 -0.4498 0.128 Uiso 1 1 calc R . . H12C H -0.5720 -0.4505 -0.4065 0.128 Uiso 1 1 calc R . . N2 N -0.1156(7) -0.4212(6) -0.4013(4) 0.0512(15) Uani 1 1 d . . . C13 C 0.0213(11) -0.4494(8) -0.4576(5) 0.064(2) Uani 1 1 d . . . H13A H -0.0381 -0.4612 -0.5279 0.096 Uiso 1 1 calc R . . H13B H 0.0879 -0.5402 -0.4332 0.096 Uiso 1 1 calc R . . H13C H 0.1065 -0.3659 -0.4497 0.096 Uiso 1 1 calc R . . C14 C -0.2007(14) -0.2735(10) -0.4247(8) 0.105(4) Uani 1 1 d . . . H14A H -0.1066 -0.1966 -0.4091 0.158 Uiso 1 1 calc R . . H14B H -0.2914 -0.2573 -0.3850 0.158 Uiso 1 1 calc R . . H14C H -0.2603 -0.2688 -0.4953 0.158 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 I1 0.0932(4) 0.0387(2) 0.0614(3) -0.0034(2) 0.0167(2) -0.0057(2) I2 0.0745(4) 0.0748(3) 0.0786(4) 0.0049(3) 0.0070(3) 0.0052(3) P1 0.0641(12) 0.0406(8) 0.0474(9) 0.0010(8) 0.0163(9) 0.0093(8) C1 0.043(4) 0.065(5) 0.046(4) 0.009(3) 0.008(3) 0.008(3) C2 0.063(5) 0.088(6) 0.081(6) 0.041(5) 0.029(5) 0.022(4) C3 0.047(5) 0.154(10) 0.060(6) 0.052(6) 0.010(4) 0.028(6) C4 0.049(5) 0.164(10) 0.050(5) 0.015(6) 0.009(4) -0.003(7) C5 0.040(4) 0.120(7) 0.042(4) 0.007(4) 0.010(3) -0.008(4) C6 0.056(5) 0.142(10) 0.053(5) -0.044(6) 0.012(4) -0.034(6) C7 0.084(7) 0.096(7) 0.082(6) -0.050(6) 0.026(6) -0.028(5) C8 0.067(5) 0.062(5) 0.070(5) -0.024(4) 0.013(4) -0.005(4) C9 0.044(4) 0.061(4) 0.047(4) -0.009(3) 0.013(3) -0.001(3) C10 0.036(4) 0.075(5) 0.034(3) -0.002(3) 0.005(3) -0.006(3) P9 0.0404(10) 0.0363(8) 0.0365(8) -0.0016(6) 0.0057(7) 0.0020(6) N1 0.035(3) 0.051(3) 0.054(3) 0.001(3) 0.013(3) 0.005(2) C11 0.067(5) 0.075(5) 0.086(6) -0.006(4) 0.038(5) -0.009(4) C12 0.047(5) 0.108(7) 0.092(6) -0.005(5) -0.004(5) -0.002(5) N2 0.054(3) 0.059(4) 0.044(3) 0.015(2) 0.017(2) 0.012(3) C13 0.074(5) 0.067(4) 0.059(4) 0.016(4) 0.032(4) 0.002(4) C14 0.125(8) 0.070(6) 0.141(9) 0.059(6) 0.075(7) 0.056(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 P1 2.495(2) . ? P1 C1 1.814(7) . ? P1 P9 2.225(2) . ? C1 C2 1.378(9) . ? C1 C10 1.419(10) . ? C2 C3 1.425(13) . ? C2 H2A 0.9500 . ? C3 C4 1.335(15) . ? C3 H3A 0.9500 . ? C4 C5 1.399(13) . ? C4 H4A 0.9500 . ? C5 C6 1.418(14) . ? C5 C10 1.428(10) . ? C6 C7 1.353(13) . ? C6 H6A 0.9500 . ? C7 C8 1.418(12) . ? C7 H7A 0.9500 . ? C8 C9 1.371(9) . ? C8 H8A 0.9500 . ? C9 C10 1.404(9) . ? C9 P9 1.787(7) . ? P9 N1 1.617(5) . ? P9 N2 1.617(5) . ? N1 C12 1.460(10) . ? N1 C11 1.463(9) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? N2 C13 1.449(8) . ? N2 C14 1.482(9) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 C1 P1 P9 89.6(2) . . ? C1 P1 I1 105.9(2) . . ? P9 P1 I1 96.53(8) . . ? C2 C1 C10 118.4(7) . . ? C2 C1 P1 123.2(6) . . ? C10 C1 P1 118.0(5) . . ? C1 C2 C3 119.5(9) . . ? C1 C2 H2A 120.3 . . ? C3 C2 H2A 120.3 . . ? C4 C3 C2 122.3(8) . . ? C4 C3 H3A 118.9 . . ? C2 C3 H3A 118.9 . . ? C3 C4 C5 120.7(9) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? C4 C5 C6 123.4(8) . . ? C4 C5 C10 118.0(9) . . ? C6 C5 C10 118.6(8) . . ? C7 C6 C5 121.3(7) . . ? C7 C6 H6A 119.4 . . ? C5 C6 H6A 119.4 . . ? C6 C7 C8 120.9(8) . . ? C6 C7 H7A 119.5 . . ? C8 C7 H7A 119.5 . . ? C9 C8 C7 118.5(9) . . ? C9 C8 H8A 120.8 . . ? C7 C8 H8A 120.8 . . ? C8 C9 C10 122.6(7) . . ? C8 C9 P9 124.4(6) . . ? C10 C9 P9 112.9(5) . . ? C9 C10 C1 120.9(6) . . ? C9 C10 C5 118.1(7) . . ? C1 C10 C5 121.0(7) . . ? N1 P9 N2 105.9(3) . . ? N1 P9 C9 108.0(3) . . ? N2 P9 C9 116.9(3) . . ? N1 P9 P1 121.2(2) . . ? N2 P9 P1 108.1(2) . . ? C9 P9 P1 97.2(2) . . ? C12 N1 C11 114.1(6) . . ? C12 N1 P9 120.1(5) . . ? C11 N1 P9 123.8(5) . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C13 N2 C14 111.5(6) . . ? C13 N2 P9 124.9(4) . . ? C14 N2 P9 121.4(5) . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 P9 P1 C1 C2 176.5(6) . . . . ? I1 P1 C1 C2 79.9(6) . . . . ? P9 P1 C1 C10 -11.4(5) . . . . ? I1 P1 C1 C10 -108.1(5) . . . . ? C10 C1 C2 C3 0.7(10) . . . . ? P1 C1 C2 C3 172.7(6) . . . . ? C1 C2 C3 C4 -2.9(12) . . . . ? C2 C3 C4 C5 2.4(13) . . . . ? C3 C4 C5 C6 -179.2(8) . . . . ? C3 C4 C5 C10 0.3(11) . . . . ? C4 C5 C6 C7 179.3(8) . . . . ? C10 C5 C6 C7 -0.2(12) . . . . ? C5 C6 C7 C8 1.7(13) . . . . ? C6 C7 C8 C9 -0.8(13) . . . . ? C7 C8 C9 C10 -1.8(11) . . . . ? C7 C8 C9 P9 -178.8(6) . . . . ? C8 C9 C10 C1 -176.0(6) . . . . ? P9 C9 C10 C1 1.3(8) . . . . ? C8 C9 C10 C5 3.3(10) . . . . ? P9 C9 C10 C5 -179.4(5) . . . . ? C2 C1 C10 C9 -178.8(6) . . . . ? P1 C1 C10 C9 8.8(8) . . . . ? C2 C1 C10 C5 1.9(9) . . . . ? P1 C1 C10 C5 -170.5(5) . . . . ? C4 C5 C10 C9 178.2(6) . . . . ? C6 C5 C10 C9 -2.2(10) . . . . ? C4 C5 C10 C1 -2.5(10) . . . . ? C6 C5 C10 C1 177.1(6) . . . . ? C8 C9 P9 N1 -64.5(7) . . . . ? C10 C9 P9 N1 118.2(5) . . . . ? C8 C9 P9 N2 54.7(7) . . . . ? C10 C9 P9 N2 -122.6(5) . . . . ? C8 C9 P9 P1 169.3(6) . . . . ? C10 C9 P9 P1 -8.0(5) . . . . ? C1 P1 P9 N1 -106.3(3) . . . . ? I1 P1 P9 N1 -0.4(2) . . . . ? C1 P1 P9 N2 131.3(3) . . . . ? I1 P1 P9 N2 -122.8(2) . . . . ? C1 P1 P9 C9 9.9(3) . . . . ? I1 P1 P9 C9 115.8(2) . . . . ? N2 P9 N1 C12 43.7(6) . . . . ? C9 P9 N1 C12 169.7(6) . . . . ? P1 P9 N1 C12 -79.7(6) . . . . ? N2 P9 N1 C11 -153.1(6) . . . . ? C9 P9 N1 C11 -27.2(6) . . . . ? P1 P9 N1 C11 83.4(6) . . . . ? N1 P9 N2 C13 -150.1(6) . . . . ? C9 P9 N2 C13 89.6(6) . . . . ? P1 P9 N2 C13 -18.7(6) . . . . ? N1 P9 N2 C14 48.5(8) . . . . ? C9 P9 N2 C14 -71.9(8) . . . . ? P1 P9 N2 C14 179.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.702 _refine_diff_density_min -0.708 _refine_diff_density_rms 0.086 # Attachment '9.cif' data_9 _database_code_depnum_ccdc_archive 'CCDC 291574' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 N2 O2 P4' _chemical_formula_sum 'C24 H24 N2 O2 P4' _chemical_formula_weight 496.33 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.520(6) _cell_length_b 7.1417(13) _cell_length_c 18.136(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.745(6) _cell_angle_gamma 90.00 _cell_volume 2257.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3208 _cell_measurement_theta_min 2.2379 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.0300 _exptl_crystal_size_min 0.0300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method ? _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.361 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8060 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7134 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0628 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.32 _reflns_number_total 2033 _reflns_number_gt 1594 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0421P)^2^+4.1518P] 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 2033 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1116 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.26067(4) 0.09928(11) 0.01697(5) 0.0172(2) Uani 1 1 d . . . P9 P 0.36599(4) 0.14476(10) 0.12141(4) 0.0160(2) Uani 1 1 d . . . O1 O 0.40363(11) 0.3298(3) 0.12510(12) 0.0210(5) Uani 1 1 d . . . N1 N 0.42616(13) -0.0304(3) 0.12668(14) 0.0181(6) Uani 1 1 d . . . C1 C 0.20277(16) 0.0766(4) 0.08124(17) 0.0161(7) Uani 1 1 d . . . C2 C 0.12460(16) 0.0524(4) 0.05397(18) 0.0197(7) Uani 1 1 d . . . H2A H 0.0977 0.0533 -0.0009 0.024 Uiso 1 1 calc R . . C3 C 0.08374(17) 0.0261(4) 0.10629(19) 0.0207(7) Uani 1 1 d . . . H3A H 0.0296 0.0104 0.0861 0.025 Uiso 1 1 calc R . . C4 C 0.12090(17) 0.0227(4) 0.18587(18) 0.0200(7) Uani 1 1 d . . . H4A H 0.0925 0.0047 0.2202 0.024 Uiso 1 1 calc R . . C5 C 0.20149(16) 0.0460(4) 0.21680(18) 0.0164(7) Uani 1 1 d . . . C6 C 0.24360(17) 0.0401(4) 0.29836(18) 0.0195(7) Uani 1 1 d . . . H6A H 0.2172 0.0226 0.3345 0.023 Uiso 1 1 calc R . . C7 C 0.32154(18) 0.0594(4) 0.32550(18) 0.0206(7) Uani 1 1 d . . . H7A H 0.3486 0.0536 0.3802 0.025 Uiso 1 1 calc R . . C8 C 0.36229(17) 0.0877(4) 0.27347(17) 0.0186(7) Uani 1 1 d . . . H8A H 0.4165 0.1012 0.2930 0.022 Uiso 1 1 calc R . . C9 C 0.32308(16) 0.0956(4) 0.19400(17) 0.0156(6) Uani 1 1 d . . . C10 C 0.24263(16) 0.0729(4) 0.16440(17) 0.0153(6) Uani 1 1 d . . . C11 C 0.40274(19) -0.2237(4) 0.1355(2) 0.0291(8) Uani 1 1 d . . . H11A H 0.3692 -0.2705 0.0847 0.044 Uiso 1 1 calc R . . H11B H 0.3751 -0.2260 0.1731 0.044 Uiso 1 1 calc R . . H11C H 0.4484 -0.3035 0.1547 0.044 Uiso 1 1 calc R . . C12 C 0.46755(18) -0.0202(4) 0.07079(19) 0.0266(8) Uani 1 1 d . . . H12A H 0.5129 -0.1013 0.0885 0.040 Uiso 1 1 calc R . . H12B H 0.4836 0.1092 0.0673 0.040 Uiso 1 1 calc R . . H12C H 0.4338 -0.0618 0.0191 0.040 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 0.0160(4) 0.0213(4) 0.0135(5) -0.0005(3) 0.0039(3) -0.0002(3) P9 0.0147(4) 0.0199(4) 0.0136(4) -0.0003(3) 0.0049(3) 0.0001(3) O1 0.0213(12) 0.0203(11) 0.0205(12) -0.0001(9) 0.0061(10) -0.0057(9) N1 0.0154(13) 0.0216(13) 0.0183(15) -0.0004(10) 0.0069(11) 0.0024(10) C1 0.0183(16) 0.0157(15) 0.0148(17) -0.0005(12) 0.0063(13) -0.0010(11) C2 0.0188(16) 0.0216(16) 0.0177(17) 0.0013(12) 0.0049(14) -0.0011(12) C3 0.0166(16) 0.0185(16) 0.027(2) 0.0020(13) 0.0073(14) -0.0001(12) C4 0.0220(17) 0.0166(16) 0.0233(19) 0.0005(13) 0.0100(15) 0.0004(12) C5 0.0196(16) 0.0120(15) 0.0178(17) 0.0027(12) 0.0066(13) 0.0024(11) C6 0.0249(18) 0.0179(16) 0.0186(18) 0.0041(12) 0.0113(14) 0.0027(12) C7 0.0269(18) 0.0203(16) 0.0129(17) 0.0011(12) 0.0046(14) 0.0006(13) C8 0.0155(16) 0.0222(16) 0.0170(17) -0.0029(12) 0.0041(14) -0.0007(12) C9 0.0178(16) 0.0161(14) 0.0126(16) 0.0010(12) 0.0049(13) 0.0019(11) C10 0.0182(16) 0.0122(14) 0.0144(17) 0.0013(12) 0.0042(13) 0.0018(11) C11 0.033(2) 0.0211(17) 0.037(2) 0.0010(14) 0.0173(17) 0.0011(14) C12 0.0249(18) 0.0345(19) 0.0235(19) 0.0009(14) 0.0121(15) 0.0039(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C1 1.838(3) . ? P1 P1 2.2373(16) 7 ? P1 P9 2.2365(12) . ? P9 O1 1.485(2) . ? P9 N1 1.657(2) . ? P9 C9 1.787(3) . ? N1 C12 1.465(4) . ? N1 C11 1.472(4) . ? C1 C2 1.374(4) . ? C1 C10 1.438(4) . ? C2 C3 1.412(4) . ? C3 C4 1.373(4) . ? C4 C5 1.416(4) . ? C5 C10 1.418(4) . ? C5 C6 1.421(4) . ? C6 C7 1.366(4) . ? C7 C8 1.408(4) . ? C8 C9 1.379(4) . ? C9 C10 1.412(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 P1 99.94(10) . 7 ? C1 P1 P9 90.26(10) . . ? P1 P1 P9 96.64(5) 7 . ? O1 P9 N1 111.91(12) . . ? O1 P9 C9 117.41(13) . . ? N1 P9 C9 105.49(13) . . ? O1 P9 P1 115.42(9) . . ? N1 P9 P1 108.44(9) . . ? C9 P9 P1 96.76(10) . . ? C12 N1 C11 111.4(2) . . ? C12 N1 P9 114.93(19) . . ? C11 N1 P9 119.8(2) . . ? C2 C1 C10 118.7(3) . . ? C2 C1 P1 123.5(2) . . ? C10 C1 P1 117.6(2) . . ? C1 C2 C3 120.9(3) . . ? C4 C3 C2 121.1(3) . . ? C3 C4 C5 120.1(3) . . ? C10 C5 C6 118.1(3) . . ? C10 C5 C4 118.9(3) . . ? C6 C5 C4 122.9(3) . . ? C7 C6 C5 120.9(3) . . ? C6 C7 C8 120.9(3) . . ? C9 C8 C7 119.6(3) . . ? C8 C9 C10 120.5(3) . . ? C8 C9 P9 124.7(2) . . ? C10 C9 P9 114.6(2) . . ? C9 C10 C5 119.8(3) . . ? C9 C10 C1 119.9(3) . . ? C5 C10 C1 120.3(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 P1 P9 O1 -117.25(13) . . . . ? P1 P1 P9 O1 -17.20(11) 7 . . . ? C1 P1 P9 N1 116.32(13) . . . . ? P1 P1 P9 N1 -143.64(10) 7 . . . ? C1 P1 P9 C9 7.47(12) . . . . ? P1 P1 P9 C9 107.52(10) 7 . . . ? O1 P9 N1 C12 -52.0(2) . . . . ? C9 P9 N1 C12 179.2(2) . . . . ? P1 P9 N1 C12 76.5(2) . . . . ? O1 P9 N1 C11 171.1(2) . . . . ? C9 P9 N1 C11 42.3(3) . . . . ? P1 P9 N1 C11 -60.5(2) . . . . ? P1 P1 C1 C2 80.2(2) 7 . . . ? P9 P1 C1 C2 177.0(2) . . . . ? P1 P1 C1 C10 -103.7(2) 7 . . . ? P9 P1 C1 C10 -6.9(2) . . . . ? C10 C1 C2 C3 0.6(4) . . . . ? P1 C1 C2 C3 176.7(2) . . . . ? C1 C2 C3 C4 -0.4(4) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C3 C4 C5 C10 0.1(4) . . . . ? C3 C4 C5 C6 -178.7(3) . . . . ? C10 C5 C6 C7 -0.2(4) . . . . ? C4 C5 C6 C7 178.6(3) . . . . ? C5 C6 C7 C8 0.7(4) . . . . ? C6 C7 C8 C9 -0.2(4) . . . . ? C7 C8 C9 C10 -0.9(4) . . . . ? C7 C8 C9 P9 176.0(2) . . . . ? O1 P9 C9 C8 -61.7(3) . . . . ? N1 P9 C9 C8 63.8(3) . . . . ? P1 P9 C9 C8 175.1(2) . . . . ? O1 P9 C9 C10 115.4(2) . . . . ? N1 P9 C9 C10 -119.1(2) . . . . ? P1 P9 C9 C10 -7.8(2) . . . . ? C8 C9 C10 C5 1.5(4) . . . . ? P9 C9 C10 C5 -175.8(2) . . . . ? C8 C9 C10 C1 -178.4(2) . . . . ? P9 C9 C10 C1 4.4(3) . . . . ? C6 C5 C10 C9 -0.9(4) . . . . ? C4 C5 C10 C9 -179.7(2) . . . . ? C6 C5 C10 C1 178.9(2) . . . . ? C4 C5 C10 C1 0.1(4) . . . . ? C2 C1 C10 C9 179.4(2) . . . . ? P1 C1 C10 C9 3.1(3) . . . . ? C2 C1 C10 C5 -0.4(4) . . . . ? P1 C1 C10 C5 -176.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.392 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.077