# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address 'Khodayar Gholivand' ;Department of Chemistry Tarbiat Modares University Tehran 14115-175, Iran ; 'Hamid R. Mahzouni' ;Department of Chemistry Tarbiat Modares University Tehran 14115-175, Iran ; 'Mehdi D. Esrafili' ;Department of Chemistry, Faculty of Basic Sciences, University of Maragheh, Maragheh, Iran ; _publ_contact_author_name 'Prof.Khodayar Gholivand' _publ_contact_author_email 'gholi kh@modares.ac.ir' _publ_contact_author_address ;Department of Chemistry Tarbiat Modares University Tehran 14115-175, Iran ; _publ_contact_author_phone +98-21-82884422 _publ_section_title ; Structure, Bonding, Electronic and Energy Aspects of a New Family of Early Lanthanide (La, Ce and Nd) Complexes with Phosphoric Triamides; Insights from Experimental and DFT Studies ; data_ClPA #TrackingRef '- Stractures.CIF' _database_code_depnum_ccdc_archive 'CCDC 292747' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H21 Cl N3 O3 P' _chemical_formula_sum 'C14 H21 Cl N3 O3 P' _chemical_formula_weight 345.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.614(3) _cell_length_b 9.3063(17) _cell_length_c 20.213(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3313.3(10) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2318 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 23.9 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.342 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17230 _diffrn_reflns_av_R_equivalents 0.0705 _diffrn_reflns_av_sigmaI/netI 0.0702 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.02 _reflns_number_total 3558 _reflns_number_gt 2024 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998b)' _computing_cell_refinement 'SAINTPlus (Bruker, 1998a)' _computing_data_reduction 'SAINTPlus (Bruker, 1998a)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998a)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998a)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998a)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998a)' _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^)+(0.0609P)^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 3558 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0922 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1219 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 0.892 _refine_ls_restrained_S_all 0.892 _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 Cl1 Cl 0.39838(5) 0.84951(8) 0.76213(4) 0.0444(2) Uani 1 1 d . . . P1 P 0.17508(4) 0.79646(7) 0.47101(3) 0.02646(19) Uani 1 1 d . . . O1 O 0.17945(10) 0.95405(17) 0.46647(8) 0.0282(4) Uani 1 1 d . . . O2 O 0.14481(13) 0.6118(2) 0.26768(10) 0.0481(6) Uani 1 1 d . . . O3 O -0.01841(11) 0.6934(2) 0.60489(10) 0.0441(6) Uani 1 1 d . . . N1 N 0.25116(13) 0.7204(2) 0.50402(11) 0.0291(5) Uani 1 1 d . . . H1A H 0.2729 0.6519 0.4808 0.035 Uiso 1 1 calc R . . N2 N 0.16298(12) 0.7269(2) 0.39658(11) 0.0287(5) Uani 1 1 d . . . N3 N 0.10397(12) 0.7420(2) 0.51745(10) 0.0274(5) Uani 1 1 d . . . C1 C 0.28474(15) 0.7537(3) 0.56519(13) 0.0272(6) Uani 1 1 d . . . C2 C 0.35110(15) 0.6838(3) 0.58472(14) 0.0297(6) Uani 1 1 d . . . H2A H 0.3733 0.6145 0.5561 0.036 Uiso 1 1 calc R . . C3 C 0.38514(16) 0.7131(3) 0.64457(14) 0.0327(7) Uani 1 1 d . . . H3A H 0.4303 0.6642 0.6568 0.039 Uiso 1 1 calc R . . C4 C 0.35403(17) 0.8127(3) 0.68641(14) 0.0336(7) Uani 1 1 d . . . C5 C 0.28792(16) 0.8845(3) 0.66897(13) 0.0319(7) Uani 1 1 d . . . H5A H 0.2665 0.9541 0.6979 0.038 Uiso 1 1 calc R . . C6 C 0.25361(16) 0.8541(3) 0.60939(13) 0.0306(6) Uani 1 1 d . . . H6A H 0.2079 0.9021 0.5979 0.037 Uiso 1 1 calc R . . C7 C 0.20249(18) 0.7891(3) 0.33985(14) 0.0398(7) Uani 1 1 d . . . H7A H 0.2536 0.7457 0.3357 0.048 Uiso 1 1 calc R . . H7B H 0.2087 0.8939 0.3464 0.048 Uiso 1 1 calc R . . C8 C 0.1573(2) 0.7615(3) 0.27757(14) 0.0441(8) Uani 1 1 d . . . H8A H 0.1078 0.8113 0.2807 0.053 Uiso 1 1 calc R . . H8B H 0.1850 0.8012 0.2391 0.053 Uiso 1 1 calc R . . C9 C 0.10331(17) 0.5542(3) 0.32221(13) 0.0379(7) Uani 1 1 d . . . H9A H 0.0944 0.4505 0.3147 0.045 Uiso 1 1 calc R . . H9B H 0.0532 0.6022 0.3248 0.045 Uiso 1 1 calc R . . C10 C 0.14468(17) 0.5741(3) 0.38719(14) 0.0336(7) Uani 1 1 d . . . H10A H 0.1124 0.5401 0.4241 0.040 Uiso 1 1 calc R . . H10B H 0.1920 0.5166 0.3871 0.040 Uiso 1 1 calc R . . C11 C 0.10220(16) 0.6172(3) 0.56034(15) 0.0368(7) Uani 1 1 d . . . H11A H 0.1546 0.5891 0.5723 0.044 Uiso 1 1 calc R . . H11B H 0.0782 0.5356 0.5369 0.044 Uiso 1 1 calc R . . C12 C 0.05771(17) 0.6515(3) 0.62232(15) 0.0427(8) Uani 1 1 d . . . H12A H 0.0562 0.5661 0.6515 0.051 Uiso 1 1 calc R . . H12B H 0.0829 0.7306 0.6467 0.051 Uiso 1 1 calc R . . C13 C -0.01575(17) 0.8210(3) 0.56583(15) 0.0402(8) Uani 1 1 d . . . H13A H 0.0097 0.8983 0.5911 0.048 Uiso 1 1 calc R . . H13B H -0.0681 0.8529 0.5557 0.048 Uiso 1 1 calc R . . C14 C 0.02658(15) 0.7947(3) 0.50234(13) 0.0315(7) Uani 1 1 d . . . H14A H -0.0008 0.7227 0.4754 0.038 Uiso 1 1 calc R . . H14B H 0.0297 0.8850 0.4766 0.038 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 Cl1 0.0553(5) 0.0457(5) 0.0323(4) 0.0015(3) -0.0094(4) -0.0061(4) P1 0.0262(4) 0.0236(4) 0.0296(4) -0.0023(3) 0.0005(3) -0.0019(3) O1 0.0311(10) 0.0234(9) 0.0300(10) -0.0019(8) 0.0034(9) -0.0040(8) O2 0.0651(15) 0.0435(13) 0.0358(12) -0.0134(10) 0.0132(11) -0.0152(11) O3 0.0322(12) 0.0557(13) 0.0445(12) 0.0198(11) 0.0055(10) 0.0045(10) N1 0.0251(12) 0.0302(13) 0.0319(12) -0.0086(10) 0.0018(10) 0.0009(10) N2 0.0282(13) 0.0239(12) 0.0342(13) -0.0021(10) 0.0012(11) -0.0019(10) N3 0.0265(13) 0.0268(12) 0.0289(12) 0.0030(10) 0.0004(10) -0.0008(9) C1 0.0236(14) 0.0250(14) 0.0330(15) -0.0001(12) 0.0036(12) -0.0052(12) C2 0.0246(15) 0.0288(15) 0.0357(16) -0.0021(12) 0.0047(13) -0.0007(12) C3 0.0284(15) 0.0301(15) 0.0397(16) 0.0005(13) -0.0004(13) 0.0005(13) C4 0.0378(17) 0.0335(16) 0.0295(15) 0.0044(13) -0.0044(13) -0.0117(13) C5 0.0349(16) 0.0303(15) 0.0305(16) -0.0021(12) 0.0036(14) -0.0030(13) C6 0.0273(15) 0.0303(15) 0.0341(15) -0.0009(12) 0.0014(13) 0.0006(12) C7 0.0431(18) 0.0380(17) 0.0381(17) -0.0052(14) 0.0089(15) -0.0107(15) C8 0.064(2) 0.0365(17) 0.0319(17) -0.0060(13) 0.0045(16) -0.0137(16) C9 0.0428(18) 0.0335(16) 0.0373(17) -0.0073(13) 0.0060(15) -0.0106(14) C10 0.0362(17) 0.0233(14) 0.0414(17) -0.0011(12) 0.0014(14) 0.0010(12) C11 0.0290(16) 0.0281(16) 0.0532(19) 0.0130(13) -0.0014(15) 0.0008(13) C12 0.0372(18) 0.051(2) 0.0403(18) 0.0190(15) -0.0007(15) -0.0009(15) C13 0.0304(16) 0.0458(19) 0.0444(18) 0.0110(14) 0.0067(14) 0.0084(14) C14 0.0256(15) 0.0341(15) 0.0349(16) 0.0093(13) -0.0034(13) 0.0041(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 Cl1 C4 1.752(3) . ? P1 O1 1.4715(18) . ? P1 N3 1.645(2) . ? P1 N2 1.652(2) . ? P1 N1 1.656(2) . ? O2 C8 1.425(4) . ? O2 C9 1.427(3) . ? O3 C13 1.427(3) . ? O3 C12 1.440(4) . ? N1 C1 1.405(3) . ? N1 H1A 0.8800 . ? N2 C7 1.461(4) . ? N2 C10 1.470(3) . ? N3 C11 1.449(3) . ? N3 C14 1.481(3) . ? C1 C2 1.395(4) . ? C1 C6 1.404(4) . ? C2 C3 1.377(4) . ? C2 H2A 0.9500 . ? C3 C4 1.369(4) . ? C3 H3A 0.9500 . ? C4 C5 1.388(4) . ? C5 C6 1.377(4) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.511(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.513(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.512(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.504(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 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 O1 P1 N3 112.49(11) . . ? O1 P1 N2 109.93(11) . . ? N3 P1 N2 107.49(11) . . ? O1 P1 N1 114.11(11) . . ? N3 P1 N1 104.75(11) . . ? N2 P1 N1 107.70(11) . . ? C8 O2 C9 109.7(2) . . ? C13 O3 C12 109.3(2) . . ? C1 N1 P1 126.96(19) . . ? C1 N1 H1A 116.5 . . ? P1 N1 H1A 116.5 . . ? C7 N2 C10 112.8(2) . . ? C7 N2 P1 119.85(18) . . ? C10 N2 P1 121.68(18) . . ? C11 N3 C14 111.7(2) . . ? C11 N3 P1 127.20(18) . . ? C14 N3 P1 118.76(17) . . ? C2 C1 C6 117.2(2) . . ? C2 C1 N1 119.9(2) . . ? C6 C1 N1 122.8(2) . . ? C3 C2 C1 121.4(3) . . ? C3 C2 H2A 119.3 . . ? C1 C2 H2A 119.3 . . ? C4 C3 C2 120.2(3) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C3 C4 C5 120.3(3) . . ? C3 C4 Cl1 119.6(2) . . ? C5 C4 Cl1 120.1(2) . . ? C6 C5 C4 119.4(3) . . ? C6 C5 H5A 120.3 . . ? C4 C5 H5A 120.3 . . ? C5 C6 C1 121.5(3) . . ? C5 C6 H6A 119.3 . . ? C1 C6 H6A 119.3 . . ? N2 C7 C8 109.6(2) . . ? N2 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N2 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? O2 C8 C7 111.4(3) . . ? O2 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? O2 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? O2 C9 C10 112.2(2) . . ? O2 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? O2 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? N2 C10 C9 109.6(2) . . ? N2 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? N2 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? N3 C11 C12 109.7(2) . . ? N3 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? N3 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? O3 C12 C11 109.7(2) . . ? O3 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? O3 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? O3 C13 C14 110.7(2) . . ? O3 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? O3 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? N3 C14 C13 109.5(2) . . ? N3 C14 H14A 109.8 . . ? C13 C14 H14A 109.8 . . ? N3 C14 H14B 109.8 . . ? C13 C14 H14B 109.8 . . ? H14A C14 H14B 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 O1 P1 N1 C1 53.7(3) . . . . ? N3 P1 N1 C1 -69.8(2) . . . . ? N2 P1 N1 C1 176.0(2) . . . . ? O1 P1 N2 C7 38.4(2) . . . . ? N3 P1 N2 C7 161.2(2) . . . . ? N1 P1 N2 C7 -86.5(2) . . . . ? O1 P1 N2 C10 -170.2(2) . . . . ? N3 P1 N2 C10 -47.4(2) . . . . ? N1 P1 N2 C10 64.9(2) . . . . ? O1 P1 N3 C11 -145.4(2) . . . . ? N2 P1 N3 C11 93.5(2) . . . . ? N1 P1 N3 C11 -20.9(3) . . . . ? O1 P1 N3 C14 53.7(2) . . . . ? N2 P1 N3 C14 -67.4(2) . . . . ? N1 P1 N3 C14 178.22(19) . . . . ? P1 N1 C1 C2 -177.09(19) . . . . ? P1 N1 C1 C6 4.1(4) . . . . ? C6 C1 C2 C3 -0.7(4) . . . . ? N1 C1 C2 C3 -179.5(2) . . . . ? C1 C2 C3 C4 0.0(4) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C2 C3 C4 Cl1 -179.6(2) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? Cl1 C4 C5 C6 -179.8(2) . . . . ? C4 C5 C6 C1 -1.2(4) . . . . ? C2 C1 C6 C5 1.2(4) . . . . ? N1 C1 C6 C5 -179.9(2) . . . . ? C10 N2 C7 C8 53.4(3) . . . . ? P1 N2 C7 C8 -152.8(2) . . . . ? C9 O2 C8 C7 60.4(3) . . . . ? N2 C7 C8 O2 -57.3(3) . . . . ? C8 O2 C9 C10 -59.4(3) . . . . ? C7 N2 C10 C9 -52.1(3) . . . . ? P1 N2 C10 C9 154.6(2) . . . . ? O2 C9 C10 N2 54.8(3) . . . . ? C14 N3 C11 C12 -55.1(3) . . . . ? P1 N3 C11 C12 142.9(2) . . . . ? C13 O3 C12 C11 -62.5(3) . . . . ? N3 C11 C12 O3 59.0(3) . . . . ? C12 O3 C13 C14 62.1(3) . . . . ? C11 N3 C14 C13 54.0(3) . . . . ? P1 N3 C14 C13 -142.2(2) . . . . ? O3 C13 C14 N3 -57.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.02 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.527 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.073 data_BrPA #TrackingRef '- Stractures.CIF' _database_code_depnum_ccdc_archive 'CCDC 604114' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H21 Br N3 O3 P' _chemical_formula_sum 'C14 H21 Br N3 O3 P' _chemical_formula_weight 390.22 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' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.636(3) _cell_length_b 9.4540(15) _cell_length_c 20.571(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3429.9(9) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3593 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 40.9 _exptl_crystal_description prizm _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 2.505 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.529 _exptl_absorpt_correction_T_max 0.687 _exptl_absorpt_process_details 'SADABS (Sheldric, 1998a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30776 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.0668 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3716 _reflns_number_gt 1725 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998b)' _computing_cell_refinement 'SAINTPlus (Bruker, 1998a)' _computing_data_reduction 'SAINTPlus (Bruker, 1998a)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _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^)+(0.0120P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3716 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0937 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0534 _refine_ls_wR_factor_gt 0.0488 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _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 Br1 Br 0.095082(18) 0.34475(3) 0.236360(14) 0.08307(14) Uani 1 1 d . . . P1 P 0.32368(4) 0.29381(7) 0.52712(3) 0.04405(18) Uani 1 1 d . . . O1 O 0.31910(8) 0.44859(15) 0.53091(7) 0.0505(4) Uani 1 1 d . . . O2 O 0.51745(11) 0.1930(2) 0.39728(9) 0.0898(7) Uani 1 1 d . . . O3 O 0.34932(12) 0.1144(2) 0.72603(10) 0.0983(7) Uani 1 1 d . . . N1 N 0.24819(10) 0.21929(19) 0.49488(9) 0.0479(5) Uani 1 1 d . . . H1N H 0.2317 0.1374 0.5122 0.057 Uiso 1 1 d R . . N2 N 0.39513(10) 0.24058(19) 0.48248(9) 0.0453(5) Uani 1 1 d . . . N3 N 0.33433(11) 0.2262(2) 0.59984(9) 0.0489(6) Uani 1 1 d . . . C1 C 0.14909(14) 0.1790(3) 0.41623(13) 0.0530(7) Uani 1 1 d . . . H1B H 0.1285 0.1109 0.4436 0.064 Uiso 1 1 calc R . . C2 C 0.11475(15) 0.2078(3) 0.35789(14) 0.0600(8) Uani 1 1 d . . . H2A H 0.0711 0.1588 0.3461 0.072 Uiso 1 1 calc R . . C3 C 0.14412(16) 0.3081(3) 0.31685(12) 0.0553(7) Uani 1 1 d . . . C4 C 0.20890(16) 0.3791(3) 0.33383(12) 0.0561(7) Uani 1 1 d . . . H4A H 0.2295 0.4463 0.3059 0.067 Uiso 1 1 calc R . . C5 C 0.24326(14) 0.3508(2) 0.39219(12) 0.0502(7) Uani 1 1 d . . . H5A H 0.2870 0.3999 0.4035 0.060 Uiso 1 1 calc R . . C6 C 0.21443(14) 0.2507(3) 0.43477(13) 0.0434(6) Uani 1 1 d . . . C7 C 0.39810(15) 0.1162(3) 0.44089(14) 0.0671(8) Uani 1 1 d . . . H7A H 0.3471 0.0883 0.4288 0.081 Uiso 1 1 calc R . . H7B H 0.4213 0.0383 0.4643 0.081 Uiso 1 1 calc R . . C8 C 0.44314(18) 0.1481(3) 0.38123(14) 0.0904(10) Uani 1 1 d . . . H8A H 0.4459 0.0642 0.3542 0.109 Uiso 1 1 calc R . . H8B H 0.4179 0.2217 0.3565 0.109 Uiso 1 1 calc R . . C9 C 0.51377(16) 0.3185(3) 0.43441(14) 0.0838(10) Uani 1 1 d . . . H9A H 0.4889 0.3918 0.4093 0.101 Uiso 1 1 calc R . . H9B H 0.5647 0.3504 0.4443 0.101 Uiso 1 1 calc R . . C10 C 0.47129(13) 0.2953(3) 0.49628(12) 0.0603(8) Uani 1 1 d . . . H10A H 0.4986 0.2285 0.5233 0.072 Uiso 1 1 calc R . . H10B H 0.4673 0.3839 0.5198 0.072 Uiso 1 1 calc R . . C11 C 0.35277(15) 0.0783(3) 0.60994(13) 0.0630(8) Uani 1 1 d . . . H11A H 0.3857 0.0457 0.5753 0.076 Uiso 1 1 calc R . . H11B H 0.3067 0.0223 0.6089 0.076 Uiso 1 1 calc R . . C12 C 0.39142(17) 0.0592(3) 0.67394(14) 0.0788(9) Uani 1 1 d . . . H12A H 0.4000 -0.0409 0.6813 0.095 Uiso 1 1 calc R . . H12B H 0.4405 0.1055 0.6725 0.095 Uiso 1 1 calc R . . C13 C 0.3367(2) 0.2597(3) 0.71638(14) 0.0992(12) Uani 1 1 d . . . H13A H 0.3851 0.3086 0.7151 0.119 Uiso 1 1 calc R . . H13B H 0.3079 0.2971 0.7527 0.119 Uiso 1 1 calc R . . C14 C 0.29498(17) 0.2869(3) 0.65518(14) 0.0863(10) Uani 1 1 d . . . H14A H 0.2446 0.2464 0.6582 0.104 Uiso 1 1 calc R . . H14B H 0.2897 0.3881 0.6489 0.104 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 Br1 0.0978(3) 0.0949(3) 0.05649(18) -0.00405(18) -0.01882(19) 0.0100(2) P1 0.0440(4) 0.0381(4) 0.0500(4) 0.0068(3) 0.0026(4) 0.0031(4) O1 0.0616(11) 0.0338(11) 0.0560(11) 0.0081(8) 0.0052(9) 0.0077(9) O2 0.0601(15) 0.1227(19) 0.0865(15) -0.0467(14) 0.0201(12) -0.0079(14) O3 0.1309(19) 0.0970(19) 0.0669(15) 0.0301(13) 0.0234(14) 0.0360(15) N1 0.0433(13) 0.0431(13) 0.0571(14) 0.0199(11) -0.0032(11) -0.0029(11) N2 0.0376(12) 0.0457(13) 0.0525(12) -0.0085(10) 0.0013(11) -0.0038(11) N3 0.0587(15) 0.0391(13) 0.0490(14) 0.0070(11) 0.0059(12) 0.0120(11) C1 0.0396(16) 0.0499(18) 0.070(2) 0.0136(15) -0.0017(15) 0.0003(15) C2 0.0492(18) 0.0574(19) 0.073(2) 0.0027(17) -0.0095(17) -0.0047(16) C3 0.0591(19) 0.055(2) 0.0518(18) -0.0061(16) -0.0001(16) 0.0107(16) C4 0.066(2) 0.0525(19) 0.0496(18) 0.0046(14) 0.0060(16) -0.0004(16) C5 0.0480(16) 0.0488(17) 0.0539(17) 0.0064(14) -0.0032(14) -0.0067(15) C6 0.0351(16) 0.0392(17) 0.0559(18) 0.0029(14) 0.0046(15) 0.0038(13) C7 0.0531(18) 0.0534(19) 0.095(2) -0.0259(17) 0.0002(18) -0.0020(16) C8 0.074(2) 0.119(3) 0.078(2) -0.055(2) 0.004(2) -0.001(2) C9 0.068(2) 0.101(3) 0.083(2) -0.024(2) 0.0204(19) -0.028(2) C10 0.0480(18) 0.071(2) 0.062(2) -0.0186(16) 0.0071(15) -0.0105(15) C11 0.071(2) 0.0479(19) 0.071(2) 0.0151(15) -0.0080(17) -0.0008(16) C12 0.092(2) 0.070(2) 0.075(2) 0.0201(17) 0.012(2) 0.0257(19) C13 0.174(4) 0.069(3) 0.055(2) 0.0085(17) 0.020(2) 0.035(2) C14 0.101(3) 0.083(2) 0.075(2) 0.0336(19) 0.033(2) 0.042(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 Br1 C3 1.900(3) . ? P1 O1 1.4676(15) . ? P1 N2 1.6385(19) . ? P1 N3 1.6377(19) . ? P1 N1 1.6458(19) . ? O2 C8 1.417(3) . ? O2 C9 1.412(3) . ? O3 C13 1.406(3) . ? O3 C12 1.404(3) . ? N1 C6 1.404(3) . ? N1 H1N 0.9000 . ? N2 C7 1.455(3) . ? N2 C10 1.467(3) . ? N3 C11 1.450(3) . ? N3 C14 1.452(3) . ? C1 C6 1.390(3) . ? C1 C2 1.371(3) . ? C1 H1B 0.9300 . ? C2 C3 1.371(3) . ? C2 H2A 0.9300 . ? C3 C4 1.371(3) . ? C4 C5 1.371(3) . ? C4 H4A 0.9300 . ? C5 C6 1.386(3) . ? C5 H5A 0.9300 . ? C7 C8 1.493(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.493(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.494(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.481(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 N2 112.23(10) . . ? O1 P1 N3 110.31(10) . . ? N2 P1 N3 107.69(10) . . ? O1 P1 N1 113.81(10) . . ? N2 P1 N1 105.35(10) . . ? N3 P1 N1 107.08(10) . . ? C8 O2 C9 109.6(2) . . ? C13 O3 C12 109.8(2) . . ? C6 N1 P1 127.39(16) . . ? C6 N1 H1N 113.2 . . ? P1 N1 H1N 118.0 . . ? C7 N2 C10 111.46(19) . . ? C7 N2 P1 127.26(17) . . ? C10 N2 P1 119.16(16) . . ? C11 N3 C14 112.1(2) . . ? C11 N3 P1 122.21(17) . . ? C14 N3 P1 120.47(17) . . ? C6 C1 C2 120.6(2) . . ? C6 C1 H1B 119.7 . . ? C2 C1 H1B 119.7 . . ? C3 C2 C1 120.6(3) . . ? C3 C2 H2A 119.7 . . ? C1 C2 H2A 119.7 . . ? C4 C3 C2 119.8(3) . . ? C4 C3 Br1 120.8(2) . . ? C2 C3 Br1 119.4(2) . . ? C3 C4 C5 119.7(2) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? C4 C5 C6 121.7(2) . . ? C4 C5 H5A 119.2 . . ? C6 C5 H5A 119.2 . . ? C1 C6 N1 119.3(2) . . ? C1 C6 C5 117.6(2) . . ? N1 C6 C5 123.1(2) . . ? N2 C7 C8 109.8(2) . . ? N2 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? N2 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? O2 C8 C7 111.2(2) . . ? O2 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? O2 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? O2 C9 C10 111.2(2) . . ? O2 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? O2 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? N2 C10 C9 110.3(2) . . ? N2 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? N2 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? N3 C11 C12 110.2(2) . . ? N3 C11 H11A 109.6 . . ? C12 C11 H11A 109.6 . . ? N3 C11 H11B 109.6 . . ? C12 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? O3 C12 C11 112.7(2) . . ? O3 C12 H12A 109.0 . . ? C11 C12 H12A 109.0 . . ? O3 C12 H12B 109.0 . . ? C11 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? O3 C13 C14 111.6(3) . . ? O3 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? O3 C13 H13B 109.3 . . ? C14 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? N3 C14 C13 111.1(2) . . ? N3 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? N3 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? 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 O1 P1 N1 C6 53.5(2) . . . . ? N2 P1 N1 C6 -69.9(2) . . . . ? N3 P1 N1 C6 175.64(18) . . . . ? O1 P1 N2 C7 -145.9(2) . . . . ? N3 P1 N2 C7 92.5(2) . . . . ? N1 P1 N2 C7 -21.5(2) . . . . ? O1 P1 N2 C10 52.1(2) . . . . ? N3 P1 N2 C10 -69.4(2) . . . . ? N1 P1 N2 C10 176.51(18) . . . . ? O1 P1 N3 C11 -169.74(18) . . . . ? N2 P1 N3 C11 -47.0(2) . . . . ? N1 P1 N3 C11 65.9(2) . . . . ? O1 P1 N3 C14 37.8(2) . . . . ? N2 P1 N3 C14 160.6(2) . . . . ? N1 P1 N3 C14 -86.5(2) . . . . ? C6 C1 C2 C3 -0.2(4) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? C1 C2 C3 Br1 179.87(18) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? Br1 C3 C4 C5 -179.98(18) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C2 C1 C6 N1 179.8(2) . . . . ? C2 C1 C6 C5 -0.3(4) . . . . ? P1 N1 C6 C1 -178.16(17) . . . . ? P1 N1 C6 C5 2.0(3) . . . . ? C4 C5 C6 C1 0.2(4) . . . . ? C4 C5 C6 N1 -179.9(2) . . . . ? C10 N2 C7 C8 -53.3(3) . . . . ? P1 N2 C7 C8 143.6(2) . . . . ? C9 O2 C8 C7 -61.4(3) . . . . ? N2 C7 C8 O2 57.7(3) . . . . ? C8 O2 C9 C10 60.7(3) . . . . ? C7 N2 C10 C9 52.8(3) . . . . ? P1 N2 C10 C9 -142.51(19) . . . . ? O2 C9 C10 N2 -56.4(3) . . . . ? C14 N3 C11 C12 -50.3(3) . . . . ? P1 N3 C11 C12 155.18(19) . . . . ? C13 O3 C12 C11 -59.1(3) . . . . ? N3 C11 C12 O3 54.6(3) . . . . ? C12 O3 C13 C14 59.3(3) . . . . ? C11 N3 C14 C13 51.6(3) . . . . ? P1 N3 C14 C13 -153.4(2) . . . . ? O3 C13 C14 N3 -56.1(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1N O1 8_655 0.90 2.03 2.917(2) 166 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.510 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.044 _publ_section_references ; Bruker (1998a). SAINTPlus, v. 6.01, Data Reduction and Correction Program, Bruker AXS, Madison, Wisconsin, USA. Bruker (1998b). SMART, v. 5.059, Bruker Molecular Analysis Research Tool, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (1998a). SADABS, v. 2.01, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (1998b). SHELXTL, v. 5.10, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; The hydrogen atoms of NH groups were found in the difference Fourier synthesis. The H(C) atom positions were calculated. All the hydrogen atoms were refined in isotropic approximatiom within riding model with the Uiso(H) parameters equal to 1.2 Ueq(Ci), 1.2 Ueq(Nj) where U(Ci) are the equivalent thermal parameters of the carbon atoms to which corresponding H atoms are bonded; U(Nj) are the equivalent thermal parameters of the corresponding nitrogen atom ; # start Validation Reply Form _vrf_PLAT230_26b ; PROBLEM: Hirshfeld Test Diff for C11 -- C12 .. 7.11 su RESPONSE: The C11 and C12 atoms belong to the morpholine fragment that is strongly librating in a crystal. However, we were unable to model the corresponding disorder, because the positions of two components were too close to each other. ; # Attachment '- Stractures.CIF' # Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 #TrackingRef '- Stractures.CIF' data_FPA #TrackingRef '- Stractures.CIF' _database_code_depnum_ccdc_archive 'CCDC 621185' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H21 F N3 O3 P' _chemical_formula_sum 'C14 H21 F N3 O3 P' _chemical_formula_weight 329.31 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' 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' F F 0.0171 0.0103 '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 5.387(2) _cell_length_b 10.990(4) _cell_length_c 13.749(5) _cell_angle_alpha 87.02(3) _cell_angle_beta 81.81(3) _cell_angle_gamma 83.58(3) _cell_volume 800.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8798 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 29.13 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.953 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'IPDS II (Stoe)' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8798 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 29.13 _reflns_number_total 4240 _reflns_number_gt 3599 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Step32 1.07e (Stoe & Cie GmbH, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0727P)^2^+0.1159P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4240 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.009 _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 C1 C 0.8612(2) 0.37532(11) 0.76152(9) 0.0286(2) Uani 1 1 d . . . C2 C 0.6985(3) 0.32713(13) 0.70700(10) 0.0352(3) Uani 1 1 d . . . H2 H 0.5661 0.3777 0.6849 0.042 Uiso 1 1 calc R . . C3 C 0.7339(3) 0.20317(14) 0.68544(11) 0.0396(3) Uani 1 1 d . . . H3 H 0.6261 0.1704 0.6490 0.048 Uiso 1 1 calc R . . C4 C 0.9295(3) 0.13086(13) 0.71874(12) 0.0404(3) Uani 1 1 d . . . C5 C 1.0919(3) 0.17456(14) 0.77330(13) 0.0444(3) Uani 1 1 d . . . H5 H 1.2226 0.1229 0.7955 0.053 Uiso 1 1 calc R . . C6 C 1.0566(3) 0.29779(13) 0.79459(11) 0.0377(3) Uani 1 1 d . . . H6 H 1.1650 0.3291 0.8315 0.045 Uiso 1 1 calc R . . C7 C 0.7145(5) 0.62167(18) 0.59052(12) 0.0622(5) Uani 1 1 d . . . H7A H 0.5850 0.5774 0.5708 0.075 Uiso 1 1 calc R . . H7B H 0.8588 0.5632 0.5997 0.075 Uiso 1 1 calc R . . C8 C 0.7905(5) 0.7152(2) 0.51163(15) 0.0763(7) Uani 1 1 d . . . H8A H 0.9323 0.7527 0.5287 0.092 Uiso 1 1 calc R . . H8B H 0.8454 0.6743 0.4502 0.092 Uiso 1 1 calc R . . C9 C 0.5074(5) 0.8677(2) 0.58648(14) 0.0715(6) Uani 1 1 d . . . H9A H 0.3695 0.9294 0.5758 0.086 Uiso 1 1 calc R . . H9B H 0.6423 0.9091 0.6052 0.086 Uiso 1 1 calc R . . C10 C 0.4195(4) 0.7811(2) 0.66812(14) 0.0625(5) Uani 1 1 d . . . H10A H 0.3723 0.8252 0.7285 0.075 Uiso 1 1 calc R . . H10B H 0.2717 0.7469 0.6531 0.075 Uiso 1 1 calc R . . C11 C 0.5225(4) 0.67920(14) 0.97245(10) 0.0436(4) Uani 1 1 d . . . H11A H 0.6503 0.6268 1.0022 0.052 Uiso 1 1 calc R . . H11B H 0.3712 0.6375 0.9787 0.052 Uiso 1 1 calc R . . C12 C 0.4665(4) 0.79923(17) 1.02382(11) 0.0512(4) Uani 1 1 d . . . H12A H 0.3297 0.8484 0.9968 0.061 Uiso 1 1 calc R . . H12B H 0.4118 0.7833 1.0932 0.061 Uiso 1 1 calc R . . C13 C 0.7599(4) 0.89260(14) 0.91225(12) 0.0459(4) Uani 1 1 d . . . H13A H 0.9046 0.9390 0.9060 0.055 Uiso 1 1 calc R . . H13B H 0.6254 0.9427 0.8845 0.055 Uiso 1 1 calc R . . C14 C 0.8294(3) 0.77682(14) 0.85555(12) 0.0398(3) Uani 1 1 d . . . H14A H 0.8762 0.7974 0.7864 0.048 Uiso 1 1 calc R . . H14B H 0.9726 0.7293 0.8795 0.048 Uiso 1 1 calc R . . N1 N 0.8381(2) 0.50021(10) 0.78432(10) 0.0343(3) Uani 1 1 d . . . H1 H 0.967(4) 0.5216(19) 0.7978(14) 0.047(5) Uiso 1 1 d . . . N2 N 0.6193(2) 0.68127(11) 0.68222(8) 0.0373(3) Uani 1 1 d . . . N3 N 0.6124(2) 0.70431(10) 0.86803(8) 0.0303(2) Uani 1 1 d . . . O1 O 0.34872(18) 0.54410(9) 0.81314(8) 0.0385(2) Uani 1 1 d . . . O2 O 0.5947(3) 0.80695(16) 0.49810(9) 0.0693(4) Uani 1 1 d . . . O3 O 0.6800(3) 0.86598(11) 1.01328(8) 0.0515(3) Uani 1 1 d . . . P1 P 0.58656(6) 0.60139(3) 0.78837(2) 0.02722(10) Uani 1 1 d . . . F1 F 0.9655(2) 0.00949(9) 0.69699(10) 0.0641(3) 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 C1 0.0257(6) 0.0283(6) 0.0312(5) -0.0019(4) -0.0017(4) -0.0030(4) C2 0.0345(7) 0.0340(7) 0.0385(6) -0.0037(5) -0.0108(5) -0.0008(5) C3 0.0438(8) 0.0380(7) 0.0395(7) -0.0096(6) -0.0072(6) -0.0094(6) C4 0.0436(8) 0.0269(6) 0.0487(8) -0.0062(5) 0.0025(6) -0.0042(6) C5 0.0365(7) 0.0325(7) 0.0637(10) 0.0013(6) -0.0108(7) 0.0025(6) C6 0.0331(7) 0.0332(7) 0.0489(8) -0.0010(6) -0.0132(6) -0.0028(5) C7 0.0940(16) 0.0544(10) 0.0326(7) -0.0081(7) 0.0023(8) 0.0058(10) C8 0.0918(17) 0.0842(15) 0.0405(9) 0.0086(9) 0.0136(10) 0.0116(13) C9 0.0920(17) 0.0661(13) 0.0478(9) 0.0149(9) -0.0087(10) 0.0200(12) C10 0.0589(11) 0.0727(12) 0.0456(9) 0.0138(8) -0.0021(8) 0.0245(10) C11 0.0628(10) 0.0408(7) 0.0274(6) 0.0026(5) -0.0025(6) -0.0125(7) C12 0.0668(11) 0.0547(10) 0.0298(6) -0.0089(6) 0.0040(7) -0.0070(8) C13 0.0575(10) 0.0348(7) 0.0462(8) -0.0098(6) -0.0025(7) -0.0105(7) C14 0.0358(7) 0.0364(7) 0.0471(8) -0.0112(6) 0.0015(6) -0.0086(6) N1 0.0251(5) 0.0281(5) 0.0517(7) -0.0076(5) -0.0109(5) -0.0019(4) N2 0.0422(7) 0.0391(6) 0.0276(5) -0.0016(4) -0.0024(5) 0.0056(5) N3 0.0350(6) 0.0287(5) 0.0269(5) -0.0036(4) 0.0003(4) -0.0061(4) O1 0.0268(5) 0.0384(5) 0.0512(6) -0.0048(4) -0.0056(4) -0.0058(4) O2 0.0830(11) 0.0871(10) 0.0344(6) 0.0126(6) -0.0116(6) 0.0045(8) O3 0.0711(8) 0.0484(6) 0.0381(5) -0.0123(5) -0.0119(5) -0.0095(6) P1 0.02535(17) 0.02668(16) 0.02961(16) -0.00312(11) -0.00414(11) -0.00124(11) F1 0.0732(8) 0.0291(5) 0.0888(8) -0.0160(5) -0.0052(6) -0.0012(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.3915(19) . ? C1 C2 1.3937(19) . ? C1 N1 1.4117(17) . ? C2 C3 1.396(2) . ? C2 H2 0.9300 . ? C3 C4 1.365(2) . ? C3 H3 0.9300 . ? C4 F1 1.3687(16) . ? C4 C5 1.370(2) . ? C5 C6 1.387(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N2 1.452(2) . ? C7 C8 1.501(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O2 1.401(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O2 1.413(3) . ? C9 C10 1.493(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N2 1.474(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N3 1.4705(18) . ? C11 C12 1.509(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O3 1.418(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O3 1.420(2) . ? C13 C14 1.510(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N3 1.4724(18) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? N1 P1 1.6504(14) . ? N1 H1 0.81(2) . ? N2 P1 1.6613(13) . ? N3 P1 1.6449(12) . ? O1 P1 1.4791(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.97(12) . . ? C6 C1 N1 118.15(12) . . ? C2 C1 N1 122.88(12) . . ? C1 C2 C3 120.14(13) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 118.81(14) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 F1 118.86(14) . . ? C3 C4 C5 122.78(13) . . ? F1 C4 C5 118.36(15) . . ? C4 C5 C6 118.32(14) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C5 C6 C1 120.98(14) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? N2 C7 C8 110.14(17) . . ? N2 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? N2 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? O2 C8 C7 112.9(2) . . ? O2 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? O2 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? O2 C9 C10 111.92(19) . . ? O2 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? O2 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? N2 C10 C9 110.80(16) . . ? N2 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N3 C11 C12 108.71(12) . . ? N3 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? N3 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? O3 C12 C11 112.01(15) . . ? O3 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? O3 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? O3 C13 C14 111.37(13) . . ? O3 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? O3 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? N3 C14 C13 109.31(12) . . ? N3 C14 H14A 109.8 . . ? C13 C14 H14A 109.8 . . ? N3 C14 H14B 109.8 . . ? C13 C14 H14B 109.8 . . ? H14A C14 H14B 108.3 . . ? C1 N1 P1 128.47(10) . . ? C1 N1 H1 112.9(15) . . ? P1 N1 H1 118.7(15) . . ? C7 N2 C10 111.11(14) . . ? C7 N2 P1 121.12(12) . . ? C10 N2 P1 116.67(11) . . ? C11 N3 C14 111.65(12) . . ? C11 N3 P1 118.36(10) . . ? C14 N3 P1 121.09(9) . . ? C8 O2 C9 110.70(15) . . ? C12 O3 C13 110.10(12) . . ? O1 P1 N3 111.67(6) . . ? O1 P1 N1 112.47(7) . . ? N3 P1 N1 107.86(7) . . ? O1 P1 N2 115.95(7) . . ? N3 P1 N2 102.31(7) . . ? N1 P1 N2 105.79(7) . . ? 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 C6 C1 C2 C3 -0.6(2) . . . . ? N1 C1 C2 C3 178.89(13) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? C2 C3 C4 F1 -179.49(13) . . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C3 C4 C5 C6 -0.6(3) . . . . ? F1 C4 C5 C6 179.45(14) . . . . ? C4 C5 C6 C1 0.0(2) . . . . ? C2 C1 C6 C5 0.6(2) . . . . ? N1 C1 C6 C5 -178.95(14) . . . . ? N2 C7 C8 O2 -55.8(3) . . . . ? O2 C9 C10 N2 55.2(3) . . . . ? N3 C11 C12 O3 -57.22(19) . . . . ? O3 C13 C14 N3 56.99(19) . . . . ? C6 C1 N1 P1 -158.02(12) . . . . ? C2 C1 N1 P1 22.5(2) . . . . ? C8 C7 N2 C10 52.5(3) . . . . ? C8 C7 N2 P1 -164.87(17) . . . . ? C9 C10 N2 C7 -52.9(3) . . . . ? C9 C10 N2 P1 162.63(16) . . . . ? C12 C11 N3 C14 54.76(18) . . . . ? C12 C11 N3 P1 -157.50(12) . . . . ? C13 C14 N3 C11 -55.02(17) . . . . ? C13 C14 N3 P1 158.24(11) . . . . ? C7 C8 O2 C9 58.0(3) . . . . ? C10 C9 O2 C8 -57.5(3) . . . . ? C11 C12 O3 C13 60.13(19) . . . . ? C14 C13 O3 C12 -59.66(19) . . . . ? C11 N3 P1 O1 38.04(13) . . . . ? C14 N3 P1 O1 -177.36(11) . . . . ? C11 N3 P1 N1 -86.02(13) . . . . ? C14 N3 P1 N1 58.57(13) . . . . ? C11 N3 P1 N2 162.70(12) . . . . ? C14 N3 P1 N2 -52.71(12) . . . . ? C1 N1 P1 O1 28.18(15) . . . . ? C1 N1 P1 N3 151.76(12) . . . . ? C1 N1 P1 N2 -99.35(13) . . . . ? C7 N2 P1 O1 -84.65(17) . . . . ? C10 N2 P1 O1 56.08(16) . . . . ? C7 N2 P1 N3 153.59(16) . . . . ? C10 N2 P1 N3 -65.68(15) . . . . ? C7 N2 P1 N1 40.76(17) . . . . ? C10 N2 P1 N1 -178.51(14) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.430 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.051 # end Validation Reply Form data_LaBrPA #TrackingRef '- Stractures.CIF' _database_code_depnum_ccdc_archive 'CCDC 647433' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H50 Br2 Cl3 La N6 O8 P2' _chemical_formula_sum 'C30 H50 Br2 Cl3 La N6 O8 P2' _chemical_formula_weight 1089.78 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 14.3399(7) _cell_length_b 13.0234(7) _cell_length_c 23.8310(12) _cell_angle_alpha 90.00 _cell_angle_beta 104.727(5) _cell_angle_gamma 90.00 _cell_volume 4304.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 724 _cell_measurement_theta_min 3 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 3.160 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.477 _exptl_absorpt_correction_T_max 0.526 _exptl_absorpt_process_details 'APEX2 (Bruker, 2005)' _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 'Bruker SMART APEX2 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21968 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4685 _reflns_number_gt 4218 _reflns_threshold_expression I>2/s(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'APEX2 (Bruker, 2005)' _computing_data_reduction 'APEX2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _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^)+(0.0650P)^2^+2.2880P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4685 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0830 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 La1 La 0.0000 0.301338(15) 0.2500 0.00890(8) Uani 1 2 d S . . Cl1 Cl 0.0000 0.51474(7) 0.2500 0.0195(2) Uani 1 2 d S . . Cl2 Cl -0.11395(5) 0.13441(5) 0.19253(3) 0.01430(14) Uani 1 1 d . . . P1 P 0.22249(5) 0.34701(5) 0.18835(3) 0.01022(15) Uani 1 1 d . . . O1 O 0.13567(14) 0.32241(14) 0.20958(9) 0.0140(4) Uani 1 1 d . . . O2 O 0.34696(15) 0.07449(15) 0.12297(9) 0.0181(4) Uani 1 1 d . . . O3 O 0.13477(16) 0.54565(17) 0.03121(9) 0.0229(5) Uani 1 1 d . . . N1 N 0.30479(16) 0.41567(17) 0.23362(10) 0.0126(5) Uani 1 1 d . . . H1N H 0.3265 0.4755 0.2194 0.015 Uiso 1 1 d R . . N2 N 0.27477(16) 0.24199(17) 0.17528(10) 0.0129(5) Uani 1 1 d . . . N3 N 0.18977(16) 0.41599(17) 0.12908(10) 0.0129(5) Uani 1 1 d . . . Br1 Br 0.51144(3) 0.33654(3) 0.486606(14) 0.03090(11) Uani 1 1 d . . . C1 C 0.35252(19) 0.3934(2) 0.29185(12) 0.0123(5) Uani 1 1 d . . . C2 C 0.43056(19) 0.4542(2) 0.31927(12) 0.0146(5) Uani 1 1 d . . . H2A H 0.4519 0.5057 0.2985 0.018 Uiso 1 1 calc R . . C3 C 0.4770(2) 0.4388(2) 0.37727(13) 0.0183(6) Uani 1 1 d . . . H3A H 0.5278 0.4811 0.3958 0.022 Uiso 1 1 calc R . . C4 C 0.4467(2) 0.3594(2) 0.40740(13) 0.0183(6) Uani 1 1 d . . . C5 C 0.3705(2) 0.2968(2) 0.38045(13) 0.0182(6) Uani 1 1 d . . . H5A H 0.3511 0.2437 0.4010 0.022 Uiso 1 1 calc R . . C6 C 0.3229(2) 0.3136(2) 0.32247(12) 0.0142(5) Uani 1 1 d . . . H6A H 0.2715 0.2717 0.3042 0.017 Uiso 1 1 calc R . . C7 C 0.37920(19) 0.2283(2) 0.18379(13) 0.0157(6) Uani 1 1 d . . . H7A H 0.4055 0.1912 0.2196 0.019 Uiso 1 1 calc R . . H7B H 0.4104 0.2948 0.1867 0.019 Uiso 1 1 calc R . . C8 C 0.3991(2) 0.1691(2) 0.13338(14) 0.0189(6) Uani 1 1 d . . . H8A H 0.3814 0.2112 0.0987 0.023 Uiso 1 1 calc R . . H8B H 0.4676 0.1548 0.1413 0.023 Uiso 1 1 calc R . . C9 C 0.2455(2) 0.0905(2) 0.11329(13) 0.0187(6) Uani 1 1 d . . . H9A H 0.2126 0.0248 0.1072 0.022 Uiso 1 1 calc R . . H9B H 0.2223 0.1314 0.0785 0.022 Uiso 1 1 calc R . . C10 C 0.2218(2) 0.1442(2) 0.16382(13) 0.0170(6) Uani 1 1 d . . . H10A H 0.1530 0.1572 0.1553 0.020 Uiso 1 1 calc R . . H10B H 0.2394 0.1007 0.1980 0.020 Uiso 1 1 calc R . . C11 C 0.1280(2) 0.5068(2) 0.12960(12) 0.0153(5) Uani 1 1 d . . . H11A H 0.1674 0.5658 0.1452 0.018 Uiso 1 1 calc R . . H11B H 0.0841 0.4936 0.1538 0.018 Uiso 1 1 calc R . . C12 C 0.0717(2) 0.5278(2) 0.06790(13) 0.0208(6) Uani 1 1 d . . . H12A H 0.0304 0.4696 0.0534 0.025 Uiso 1 1 calc R . . H12B H 0.0309 0.5875 0.0672 0.025 Uiso 1 1 calc R . . C13 C 0.1930(2) 0.4577(2) 0.03012(13) 0.0221(6) Uani 1 1 d . . . H13A H 0.2350 0.4706 0.0048 0.027 Uiso 1 1 calc R . . H13B H 0.1520 0.3998 0.0146 0.027 Uiso 1 1 calc R . . C14 C 0.2534(2) 0.4317(2) 0.09044(12) 0.0158(6) Uani 1 1 d . . . H14A H 0.2904 0.3698 0.0890 0.019 Uiso 1 1 calc R . . H14B H 0.2981 0.4872 0.1050 0.019 Uiso 1 1 calc R . . O1S O 0.09215(15) 0.37008(15) 0.34811(9) 0.0187(4) Uani 1 1 d . . . H1S H 0.1017 0.4376 0.3518 0.022 Uiso 1 1 d R . . C1S C 0.1246(4) 0.3272(3) 0.40665(17) 0.0435(10) Uani 1 1 d . . . H1SA H 0.1917 0.3422 0.4221 0.065 Uiso 1 1 calc R . . H1SB H 0.1152 0.2541 0.4051 0.065 Uiso 1 1 calc R . . H1SC H 0.0880 0.3571 0.4311 0.065 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 La1 0.00881(12) 0.00685(12) 0.01179(12) 0.000 0.00401(8) 0.000 Cl1 0.0276(5) 0.0089(4) 0.0208(5) 0.000 0.0037(4) 0.000 Cl2 0.0144(3) 0.0097(3) 0.0173(3) -0.0007(2) 0.0014(3) -0.0014(2) P1 0.0102(3) 0.0090(3) 0.0124(3) 0.0013(2) 0.0047(3) 0.0006(2) O1 0.0122(9) 0.0145(9) 0.0170(10) 0.0030(8) 0.0069(8) 0.0018(7) O2 0.0206(10) 0.0131(10) 0.0214(10) -0.0016(8) 0.0068(9) 0.0044(8) O3 0.0271(11) 0.0265(12) 0.0161(10) 0.0075(9) 0.0074(9) 0.0080(9) N1 0.0147(11) 0.0077(10) 0.0158(11) 0.0018(9) 0.0047(9) -0.0020(8) N2 0.0105(11) 0.0100(11) 0.0190(12) -0.0019(9) 0.0054(9) -0.0018(9) N3 0.0138(11) 0.0118(11) 0.0148(11) 0.0034(9) 0.0067(9) 0.0025(9) Br1 0.0357(2) 0.0319(2) 0.01805(18) 0.00006(13) -0.00613(14) 0.00350(14) C1 0.0128(13) 0.0089(12) 0.0158(13) -0.0003(10) 0.0047(11) 0.0043(10) C2 0.0122(13) 0.0120(13) 0.0203(14) -0.0016(11) 0.0055(11) -0.0017(10) C3 0.0117(13) 0.0178(14) 0.0244(15) -0.0045(12) 0.0024(11) 0.0015(11) C4 0.0168(14) 0.0193(15) 0.0160(14) -0.0023(11) -0.0010(11) 0.0061(11) C5 0.0200(15) 0.0137(14) 0.0201(15) 0.0022(11) 0.0036(12) 0.0026(11) C6 0.0154(13) 0.0095(12) 0.0177(14) -0.0003(10) 0.0041(11) -0.0026(10) C7 0.0108(13) 0.0117(13) 0.0248(15) -0.0010(11) 0.0048(11) 0.0016(10) C8 0.0184(15) 0.0153(14) 0.0254(16) -0.0005(12) 0.0100(13) 0.0046(11) C9 0.0173(14) 0.0167(14) 0.0211(14) -0.0047(12) 0.0032(12) -0.0018(11) C10 0.0203(14) 0.0093(13) 0.0235(15) -0.0036(11) 0.0095(12) -0.0037(11) C11 0.0163(13) 0.0135(13) 0.0166(13) 0.0027(11) 0.0051(11) 0.0043(10) C12 0.0159(14) 0.0253(16) 0.0195(15) 0.0046(12) 0.0017(12) 0.0049(12) C13 0.0289(16) 0.0236(16) 0.0153(14) 0.0019(12) 0.0085(12) 0.0042(13) C14 0.0171(14) 0.0157(13) 0.0166(14) 0.0036(11) 0.0078(11) 0.0031(11) O1S 0.0241(11) 0.0108(10) 0.0192(10) -0.0027(8) 0.0019(9) -0.0016(8) C1S 0.064(3) 0.034(2) 0.032(2) -0.0060(16) 0.011(2) 0.0099(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 La1 O1 2.3960(19) . ? La1 O1 2.3960(19) 2 ? La1 O1S 2.538(2) . ? La1 O1S 2.538(2) 2 ? La1 Cl1 2.7792(10) . ? La1 Cl2 2.8520(7) . ? La1 Cl2 2.8520(7) 2 ? P1 O1 1.4930(19) . ? P1 N2 1.627(2) . ? P1 N3 1.639(2) . ? P1 N1 1.646(2) . ? O2 C8 1.429(4) . ? O2 C9 1.430(3) . ? O3 C13 1.421(4) . ? O3 C12 1.428(4) . ? N1 C1 1.412(3) . ? N1 H1N 0.9337 . ? N2 C7 1.470(3) . ? N2 C10 1.473(3) . ? N3 C14 1.466(3) . ? N3 C11 1.480(3) . ? Br1 C4 1.903(3) . ? C1 C2 1.390(4) . ? C1 C6 1.398(4) . ? C2 C3 1.388(4) . ? C2 H2A 0.9300 . ? C3 C4 1.390(4) . ? C3 H3A 0.9300 . ? C4 C5 1.383(4) . ? C5 C6 1.394(4) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.514(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.504(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.512(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.516(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? O1S C1S 1.464(4) . ? O1S H1S 0.8906 . ? C1S H1SA 0.9600 . ? C1S H1SB 0.9600 . ? C1S H1SC 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 La1 O1 166.85(9) . 2 ? O1 La1 O1S 92.53(7) . . ? O1 La1 O1S 82.82(7) 2 . ? O1 La1 O1S 82.82(7) . 2 ? O1 La1 O1S 92.53(7) 2 2 ? O1S La1 O1S 138.69(9) . 2 ? O1 La1 Cl1 83.42(5) . . ? O1 La1 Cl1 83.42(5) 2 . ? O1S La1 Cl1 69.35(5) . . ? O1S La1 Cl1 69.35(5) 2 . ? O1 La1 Cl2 108.59(5) . . ? O1 La1 Cl2 81.70(5) 2 . ? O1S La1 Cl2 144.26(5) . . ? O1S La1 Cl2 74.10(5) 2 . ? Cl1 La1 Cl2 139.664(13) . . ? O1 La1 Cl2 81.70(5) . 2 ? O1 La1 Cl2 108.59(5) 2 2 ? O1S La1 Cl2 74.10(5) . 2 ? O1S La1 Cl2 144.26(5) 2 2 ? Cl1 La1 Cl2 139.664(13) . 2 ? Cl2 La1 Cl2 80.67(3) . 2 ? O1 P1 N2 110.42(11) . . ? O1 P1 N3 109.21(12) . . ? N2 P1 N3 109.92(12) . . ? O1 P1 N1 114.53(12) . . ? N2 P1 N1 107.08(12) . . ? N3 P1 N1 105.52(12) . . ? P1 O1 La1 173.27(13) . . ? C8 O2 C9 111.6(2) . . ? C13 O3 C12 110.3(2) . . ? C1 N1 P1 128.33(19) . . ? C1 N1 H1N 113.8 . . ? P1 N1 H1N 117.7 . . ? C7 N2 C10 112.3(2) . . ? C7 N2 P1 125.34(18) . . ? C10 N2 P1 121.45(18) . . ? C14 N3 C11 111.3(2) . . ? C14 N3 P1 122.04(18) . . ? C11 N3 P1 118.15(18) . . ? C2 C1 C6 119.6(3) . . ? C2 C1 N1 118.4(2) . . ? C6 C1 N1 122.0(2) . . ? C3 C2 C1 120.7(3) . . ? C3 C2 H2A 119.6 . . ? C1 C2 H2A 119.6 . . ? C2 C3 C4 119.2(3) . . ? C2 C3 H3A 120.4 . . ? C4 C3 H3A 120.4 . . ? C5 C4 C3 120.8(3) . . ? C5 C4 Br1 119.8(2) . . ? C3 C4 Br1 119.4(2) . . ? C4 C5 C6 119.9(3) . . ? C4 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? C5 C6 C1 119.8(3) . . ? C5 C6 H6A 120.1 . . ? C1 C6 H6A 120.1 . . ? N2 C7 C8 110.1(2) . . ? N2 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? N2 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.2 . . ? O2 C8 C7 112.4(2) . . ? O2 C8 H8A 109.1 . . ? C7 C8 H8A 109.1 . . ? O2 C8 H8B 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? O2 C9 C10 111.5(2) . . ? O2 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? O2 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? N2 C10 C9 109.9(2) . . ? N2 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? N2 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? N3 C11 C12 108.0(2) . . ? N3 C11 H11A 110.1 . . ? C12 C11 H11A 110.1 . . ? N3 C11 H11B 110.1 . . ? C12 C11 H11B 110.1 . . ? H11A C11 H11B 108.4 . . ? O3 C12 C11 111.1(2) . . ? O3 C12 H12A 109.4 . . ? C11 C12 H12A 109.4 . . ? O3 C12 H12B 109.4 . . ? C11 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? O3 C13 C14 111.1(2) . . ? O3 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? O3 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? N3 C14 C13 109.3(2) . . ? N3 C14 H14A 109.8 . . ? C13 C14 H14A 109.8 . . ? N3 C14 H14B 109.8 . . ? C13 C14 H14B 109.8 . . ? H14A C14 H14B 108.3 . . ? C1S O1S La1 135.0(2) . . ? C1S O1S H1S 106.1 . . ? La1 O1S H1S 118.1 . . ? O1S C1S H1SA 109.5 . . ? O1S C1S H1SB 109.5 . . ? H1SA C1S H1SB 109.5 . . ? O1S C1S H1SC 109.5 . . ? H1SA C1S H1SC 109.5 . . ? H1SB C1S H1SC 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 O1 P1 N1 C1 56.2(3) . . . . ? N2 P1 N1 C1 -66.6(2) . . . . ? N3 P1 N1 C1 176.4(2) . . . . ? O1 P1 N2 C7 -145.9(2) . . . . ? N3 P1 N2 C7 93.5(2) . . . . ? N1 P1 N2 C7 -20.6(3) . . . . ? O1 P1 N2 C10 22.3(3) . . . . ? N3 P1 N2 C10 -98.3(2) . . . . ? N1 P1 N2 C10 147.6(2) . . . . ? O1 P1 N3 C14 -165.2(2) . . . . ? N2 P1 N3 C14 -43.9(2) . . . . ? N1 P1 N3 C14 71.2(2) . . . . ? O1 P1 N3 C11 49.6(2) . . . . ? N2 P1 N3 C11 170.90(19) . . . . ? N1 P1 N3 C11 -74.0(2) . . . . ? P1 N1 C1 C2 169.9(2) . . . . ? P1 N1 C1 C6 -10.9(4) . . . . ? C6 C1 C2 C3 -2.4(4) . . . . ? N1 C1 C2 C3 176.8(2) . . . . ? C1 C2 C3 C4 2.1(4) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C2 C3 C4 Br1 179.0(2) . . . . ? C3 C4 C5 C6 -0.4(4) . . . . ? Br1 C4 C5 C6 179.9(2) . . . . ? C4 C5 C6 C1 0.1(4) . . . . ? C2 C1 C6 C5 1.3(4) . . . . ? N1 C1 C6 C5 -177.9(2) . . . . ? C10 N2 C7 C8 52.8(3) . . . . ? P1 N2 C7 C8 -138.1(2) . . . . ? C9 O2 C8 C7 56.4(3) . . . . ? N2 C7 C8 O2 -53.3(3) . . . . ? C8 O2 C9 C10 -57.9(3) . . . . ? C7 N2 C10 C9 -54.6(3) . . . . ? P1 N2 C10 C9 135.8(2) . . . . ? O2 C9 C10 N2 56.4(3) . . . . ? C14 N3 C11 C12 56.8(3) . . . . ? P1 N3 C11 C12 -154.5(2) . . . . ? C13 O3 C12 C11 61.0(3) . . . . ? N3 C11 C12 O3 -58.7(3) . . . . ? C12 O3 C13 C14 -59.6(3) . . . . ? C11 N3 C14 C13 -56.2(3) . . . . ? P1 N3 C14 C13 156.6(2) . . . . ? O3 C13 C14 N3 57.0(3) . . . . ? O1 La1 O1S C1S -115.3(3) . . . . ? O1 La1 O1S C1S 77.0(3) 2 . . . ? O1S La1 O1S C1S 162.7(3) 2 . . . ? Cl1 La1 O1S C1S 162.7(3) . . . . ? Cl2 La1 O1S C1S 12.1(3) . . . . ? Cl2 La1 O1S C1S -34.7(3) 2 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1N Cl2 3_555 0.93 2.39 3.318(2) 174 ? O1S H1S O2 4_555 0.89 1.96 2.832(3) 164 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.194 _refine_diff_density_min -0.834 _refine_diff_density_rms 0.093 _publ_section_references ; Bruker (2005). APEX2 softwarwe package, Bruker AXS Inc., 5465, East Cheryl Parkway, Madison, WI 5317. Sheldrick G.M. (1998). SHELXTL v. 5.10, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; The hydrogen atoms of NH and OH groups were found in difference Fourier synthesis. The H(C) atom positions were calculated. All hydrogen atoms were refined in isotropic approximation in riding model with the Uiso(H) parameters equal to 1.2 Ueq(Ci), for methyl groups equal to 1.5 Ueq(Cii), where U(Ci) and U(Cii) are respectively the equivalent thermal parameters of the carbon atoms to which corresponding H atoms are bonded. There is a high positive residual density of 2.19 e\%A^-3^ near the H1S center due to considerable absorption effects which could not be completely corrected. ; # end Validation Reply Form data_CeHPA #TrackingRef '- Stractures.CIF' _database_code_depnum_ccdc_archive 'CCDC 678073' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H48 Ce Cl3 N6 O8 P2' _chemical_formula_sum 'C28 H48 Ce Cl3 N6 O8 P2' _chemical_formula_weight 905.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'F d d 2' _space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 14.3830(6) _cell_length_b 39.8715(16) _cell_length_c 12.9627(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7433.7(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6680 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3688 _exptl_absorpt_coefficient_mu 1.580 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.882 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_process_details 'APEX2 (Bruker, 2005)' _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 'Bruker SMART APEX2 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14337 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -54 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 28.98 _reflns_number_total 4942 _reflns_number_gt 4666 _reflns_threshold_expression I>2u(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'APEX2 (Bruker, 2005)' _computing_data_reduction 'APEX2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _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^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _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 -0.009(7) _refine_ls_number_reflns 4942 _refine_ls_number_parameters 218 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0234 _refine_ls_R_factor_gt 0.0210 _refine_ls_wR_factor_ref 0.0428 _refine_ls_wR_factor_gt 0.0420 _refine_ls_goodness_of_fit_ref 0.948 _refine_ls_restrained_S_all 0.948 _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 Ce1 Ce 0.0000 0.0000 0.010497(10) 0.00958(4) Uani 1 2 d S . . Cl1 Cl -0.08176(4) 0.036026(14) -0.15739(4) 0.01558(11) Uani 1 1 d . . . Cl2 Cl 0.0000 0.0000 0.22424(6) 0.02121(17) Uani 1 2 d S . . P1 P 0.24223(4) 0.039071(14) 0.05076(4) 0.01106(11) Uani 1 1 d . . . O1 O 0.14663(10) 0.02669(4) 0.02657(12) 0.0151(3) Uani 1 1 d . . . O2 O 0.21594(11) 0.13216(4) 0.24104(12) 0.0214(4) Uani 1 1 d . . . O3 O 0.38798(10) 0.07558(4) -0.22672(12) 0.0172(3) Uani 1 1 d . . . N1 N 0.30578(12) 0.01392(4) 0.12214(14) 0.0135(4) Uani 1 1 d . . . H1 H 0.3302 0.0204 0.1771 0.016 Uiso 1 1 d R . . N2 N 0.23266(12) 0.07446(5) 0.11581(14) 0.0135(4) Uani 1 1 d . . . N3 N 0.29912(12) 0.04440(5) -0.05622(14) 0.0129(4) Uani 1 1 d . . . C1 C 0.33090(14) -0.01951(5) 0.09498(17) 0.0125(4) Uani 1 1 d . . . C2 C 0.40138(15) -0.03537(6) 0.15094(17) 0.0150(5) Uani 1 1 d . . . H2A H 0.4337 -0.0237 0.2038 0.018 Uiso 1 1 calc R . . C3 C 0.42351(17) -0.06841(7) 0.1281(2) 0.0212(6) Uani 1 1 d . . . H3A H 0.4712 -0.0793 0.1661 0.025 Uiso 1 1 calc R . . C4 C 0.37727(17) -0.08582(6) 0.05065(18) 0.0210(5) Uani 1 1 d . . . H4A H 0.3927 -0.1085 0.0361 0.025 Uiso 1 1 calc R . . C5 C 0.30838(16) -0.06967(6) -0.00493(17) 0.0189(5) Uani 1 1 d . . . H5A H 0.2767 -0.0813 -0.0584 0.023 Uiso 1 1 calc R . . C6 C 0.28504(15) -0.03654(5) 0.01670(19) 0.0150(4) Uani 1 1 d . . . H6A H 0.2378 -0.0256 -0.0220 0.018 Uiso 1 1 calc R . . C7 C 0.16490(16) 0.07579(6) 0.20165(18) 0.0198(5) Uani 1 1 d . . . H7A H 0.1933 0.0666 0.2652 0.024 Uiso 1 1 calc R . . H7B H 0.1096 0.0621 0.1845 0.024 Uiso 1 1 calc R . . C8 C 0.13665(17) 0.11180(6) 0.2187(2) 0.0230(5) Uani 1 1 d . . . H8A H 0.1052 0.1204 0.1561 0.028 Uiso 1 1 calc R . . H8B H 0.0921 0.1130 0.2768 0.028 Uiso 1 1 calc R . . C9 C 0.28123(18) 0.13128(6) 0.15741(18) 0.0214(5) Uani 1 1 d . . . H9A H 0.3354 0.1455 0.1744 0.026 Uiso 1 1 calc R . . H9B H 0.2517 0.1404 0.0944 0.026 Uiso 1 1 calc R . . C10 C 0.31364(15) 0.09583(6) 0.13706(18) 0.0166(5) Uani 1 1 d . . . H10A H 0.3564 0.0955 0.0772 0.020 Uiso 1 1 calc R . . H10B H 0.3476 0.0872 0.1979 0.020 Uiso 1 1 calc R . . C11 C 0.25309(15) 0.04651(6) -0.15668(16) 0.0159(4) Uani 1 1 d . . . H11A H 0.1850 0.0485 -0.1469 0.019 Uiso 1 1 calc R . . H11B H 0.2656 0.0259 -0.1968 0.019 Uiso 1 1 calc R . . C12 C 0.28912(16) 0.07677(6) -0.21492(17) 0.0183(5) Uani 1 1 d . . . H12A H 0.2596 0.0776 -0.2839 0.022 Uiso 1 1 calc R . . H12B H 0.2718 0.0974 -0.1772 0.022 Uiso 1 1 calc R . . C13 C 0.43535(17) 0.07232(6) -0.12983(19) 0.0175(5) Uani 1 1 d . . . H13A H 0.4263 0.0931 -0.0892 0.021 Uiso 1 1 calc R . . H13B H 0.5028 0.0697 -0.1427 0.021 Uiso 1 1 calc R . . C14 C 0.40077(14) 0.04257(6) -0.06772(17) 0.0156(5) Uani 1 1 d . . . H14A H 0.4179 0.0215 -0.1031 0.019 Uiso 1 1 calc R . . H14B H 0.4304 0.0426 0.0012 0.019 Uiso 1 1 calc R . . O1W O -0.05709(11) 0.05502(4) 0.07611(12) 0.0174(3) Uani 1 1 d . . . H1A H -0.0637 0.0581 0.1375 0.021 Uiso 1 1 d R . . H1B H -0.0570 0.0732 0.0478 0.021 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 Ce1 0.00983(7) 0.00919(7) 0.00972(6) 0.000 0.000 -0.00056(8) Cl1 0.0173(3) 0.0167(3) 0.0127(2) 0.0013(2) -0.00061(19) 0.0023(2) Cl2 0.0370(5) 0.0160(4) 0.0106(3) 0.000 0.000 0.0080(4) P1 0.0113(3) 0.0105(3) 0.0113(2) -0.0013(2) -0.0001(2) -0.0009(2) O1 0.0128(7) 0.0144(8) 0.0180(8) -0.0034(6) 0.0001(6) -0.0017(6) O2 0.0266(8) 0.0135(8) 0.0240(9) -0.0066(6) 0.0076(7) -0.0036(6) O3 0.0183(8) 0.0204(8) 0.0129(7) 0.0014(6) 0.0019(6) -0.0023(6) N1 0.0161(9) 0.0136(9) 0.0107(8) -0.0030(7) -0.0020(7) -0.0008(7) N2 0.0113(9) 0.0135(10) 0.0156(9) -0.0051(7) 0.0018(7) -0.0023(7) N3 0.0105(9) 0.0167(10) 0.0113(8) -0.0002(7) 0.0007(7) -0.0018(7) C1 0.0128(10) 0.0118(11) 0.0130(9) 0.0025(8) 0.0039(8) -0.0010(8) C2 0.0118(11) 0.0184(12) 0.0149(11) 0.0005(8) 0.0015(8) 0.0006(9) C3 0.0159(12) 0.0258(14) 0.0220(12) 0.0087(11) 0.0038(10) 0.0041(10) C4 0.0236(12) 0.0148(12) 0.0245(11) 0.0018(9) 0.0079(10) 0.0057(10) C5 0.0233(12) 0.0174(12) 0.0159(11) -0.0028(9) 0.0029(9) -0.0011(9) C6 0.0159(10) 0.0151(11) 0.0140(10) 0.0014(10) -0.0011(10) 0.0026(8) C7 0.0210(12) 0.0184(13) 0.0199(11) -0.0060(9) 0.0092(9) -0.0057(10) C8 0.0200(12) 0.0226(13) 0.0265(12) -0.0091(10) 0.0072(10) -0.0028(10) C9 0.0263(13) 0.0171(13) 0.0208(12) -0.0034(9) 0.0082(10) -0.0039(10) C10 0.0147(11) 0.0160(12) 0.0190(10) -0.0051(9) 0.0006(9) -0.0050(9) C11 0.0175(11) 0.0178(12) 0.0124(10) -0.0002(8) -0.0030(9) -0.0031(9) C12 0.0194(11) 0.0182(12) 0.0171(11) 0.0015(9) -0.0008(9) 0.0000(9) C13 0.0163(11) 0.0202(13) 0.0160(11) -0.0017(10) 0.0013(9) -0.0041(10) C14 0.0116(10) 0.0193(12) 0.0157(10) 0.0017(9) 0.0013(9) 0.0038(9) O1W 0.0277(9) 0.0123(8) 0.0122(7) 0.0011(6) 0.0036(6) 0.0038(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 Ce1 O1 2.3713(14) 2 ? Ce1 O1 2.3713(14) . ? Ce1 O1W 2.4918(15) 2 ? Ce1 O1W 2.4918(15) . ? Ce1 Cl2 2.7706(8) . ? Ce1 Cl1 2.8605(5) . ? Ce1 Cl1 2.8605(5) 2 ? P1 O1 1.4943(15) . ? P1 N3 1.6241(18) . ? P1 N2 1.6494(19) . ? P1 N1 1.6422(19) . ? O2 C8 1.429(3) . ? O2 C9 1.435(3) . ? O3 C13 1.435(3) . ? O3 C12 1.431(3) . ? N1 C1 1.425(3) . ? N1 H1 0.8347 . ? N2 C7 1.480(3) . ? N2 C10 1.469(3) . ? N3 C11 1.463(3) . ? N3 C14 1.471(3) . ? C1 C6 1.388(3) . ? C1 C2 1.398(3) . ? C2 C3 1.387(3) . ? C2 H2A 0.9500 . ? C3 C4 1.390(4) . ? C3 H3A 0.9500 . ? C4 C5 1.384(3) . ? C4 H4A 0.9500 . ? C5 C6 1.392(3) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.508(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.511(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.515(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.517(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? O1W H1A 0.8112 . ? O1W H1B 0.8123 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ce1 O1 169.92(7) 2 . ? O1 Ce1 O1W 82.42(5) 2 2 ? O1 Ce1 O1W 94.13(5) . 2 ? O1 Ce1 O1W 94.13(5) 2 . ? O1 Ce1 O1W 82.42(5) . . ? O1W Ce1 O1W 140.09(7) 2 . ? O1 Ce1 Cl2 84.96(4) 2 . ? O1 Ce1 Cl2 84.96(4) . . ? O1W Ce1 Cl2 70.04(3) 2 . ? O1W Ce1 Cl2 70.04(3) . . ? O1 Ce1 Cl1 85.79(4) 2 . ? O1 Ce1 Cl1 101.95(4) . . ? O1W Ce1 Cl1 146.84(4) 2 . ? O1W Ce1 Cl1 71.47(4) . . ? Cl2 Ce1 Cl1 139.535(11) . . ? O1 Ce1 Cl1 101.95(4) 2 2 ? O1 Ce1 Cl1 85.79(4) . 2 ? O1W Ce1 Cl1 71.47(4) 2 2 ? O1W Ce1 Cl1 146.84(4) . 2 ? Cl2 Ce1 Cl1 139.535(11) . 2 ? Cl1 Ce1 Cl1 80.93(2) . 2 ? O1 P1 N3 109.12(9) . . ? O1 P1 N2 108.25(9) . . ? N3 P1 N2 111.51(10) . . ? O1 P1 N1 115.38(9) . . ? N3 P1 N1 106.30(9) . . ? N2 P1 N1 106.30(9) . . ? P1 O1 Ce1 170.09(10) . . ? C8 O2 C9 110.80(17) . . ? C13 O3 C12 112.42(16) . . ? C1 N1 P1 124.96(14) . . ? C1 N1 H1 113.2 . . ? P1 N1 H1 121.7 . . ? C7 N2 C10 111.11(17) . . ? C7 N2 P1 118.04(15) . . ? C10 N2 P1 121.73(14) . . ? C11 N3 C14 111.24(17) . . ? C11 N3 P1 122.65(14) . . ? C14 N3 P1 125.49(15) . . ? C6 C1 C2 120.2(2) . . ? C6 C1 N1 121.18(19) . . ? C2 C1 N1 118.61(19) . . ? C3 C2 C1 119.0(2) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C4 C3 C2 121.2(2) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C3 C4 C5 119.1(2) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? C6 C5 C4 120.6(2) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C1 C6 C5 119.8(2) . . ? C1 C6 H6A 120.1 . . ? C5 C6 H6A 120.1 . . ? N2 C7 C8 108.76(19) . . ? N2 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? N2 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? O2 C8 C7 110.8(2) . . ? O2 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? O2 C9 C10 110.89(19) . . ? O2 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? O2 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.0 . . ? N2 C10 C9 109.31(19) . . ? N2 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? N2 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? N3 C11 C12 109.54(17) . . ? N3 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? N3 C11 H11B 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.2 . . ? O3 C12 C11 111.52(18) . . ? O3 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? O3 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? O3 C13 C14 112.31(19) . . ? O3 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? O3 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? N3 C14 C13 109.92(18) . . ? N3 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? N3 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? Ce1 O1W H1A 120.6 . . ? Ce1 O1W H1B 129.1 . . ? H1A O1W H1B 107.8 . . ? 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 O1 P1 N1 C1 59.74(19) . . . . ? N3 P1 N1 C1 -61.36(18) . . . . ? N2 P1 N1 C1 179.73(16) . . . . ? O1 P1 N2 C7 45.89(18) . . . . ? N3 P1 N2 C7 165.94(16) . . . . ? N1 P1 N2 C7 -78.62(18) . . . . ? O1 P1 N2 C10 -170.12(17) . . . . ? N3 P1 N2 C10 -50.1(2) . . . . ? N1 P1 N2 C10 65.37(19) . . . . ? O1 P1 N3 C11 17.0(2) . . . . ? N2 P1 N3 C11 -102.55(18) . . . . ? N1 P1 N3 C11 142.01(17) . . . . ? O1 P1 N3 C14 -153.18(17) . . . . ? N2 P1 N3 C14 87.29(19) . . . . ? N1 P1 N3 C14 -28.2(2) . . . . ? P1 N1 C1 C6 -15.9(3) . . . . ? P1 N1 C1 C2 165.93(16) . . . . ? C6 C1 C2 C3 -1.0(3) . . . . ? N1 C1 C2 C3 177.2(2) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? C2 C3 C4 C5 0.5(4) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C2 C1 C6 C5 1.0(3) . . . . ? N1 C1 C6 C5 -177.14(19) . . . . ? C4 C5 C6 C1 -0.3(3) . . . . ? C10 N2 C7 C8 56.9(2) . . . . ? P1 N2 C7 C8 -155.47(17) . . . . ? C9 O2 C8 C7 60.0(3) . . . . ? N2 C7 C8 O2 -58.2(2) . . . . ? C8 O2 C9 C10 -59.2(3) . . . . ? C7 N2 C10 C9 -56.4(2) . . . . ? P1 N2 C10 C9 157.38(16) . . . . ? O2 C9 C10 N2 56.9(3) . . . . ? C14 N3 C11 C12 -57.5(2) . . . . ? P1 N3 C11 C12 131.10(17) . . . . ? C13 O3 C12 C11 -55.6(2) . . . . ? N3 C11 C12 O3 56.9(2) . . . . ? C12 O3 C13 C14 54.1(2) . . . . ? C11 N3 C14 C13 55.8(2) . . . . ? P1 N3 C14 C13 -133.05(18) . . . . ? O3 C13 C14 N3 -53.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 Cl1 9_555 0.84 2.57 3.400(2) 174 ? O1W H1A O3 9_455 0.81 2.02 2.798(2) 162 ? O1W H1B O2 11_454 0.81 1.95 2.757(2) 169 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.916 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.065 _publ_section_references ; Bruker (2005). APEX2 softwarwe package, Bruker AXS Inc., 5465, East Cheryl Parkway, Madison, WI 5317. Sheldrick G.M. (1998). SHELXTL v. 5.10, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; The H(C) atom positions were calculated. All H(N) and H(O) atoms were found in diffrence Fourier synthsis. All hydrogen atoms were refined in isotropic approximatiom in riding model with with the Uiso(H) parameters equal to 1.2 Ueq(Xi), where U(Xi) are the equivalent thermal parameters of the carbon and nitrogen atoms to which corresponding H atoms are bonded. ; # end Validation Reply Form data_LaClPA #TrackingRef '- Stractures.CIF' _database_code_depnum_ccdc_archive 'CCDC 678075' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H46 Cl5 La N6 O8 P2, 2(C2 H3 N)' _chemical_formula_sum 'C32 H52 Cl5 La N8 O8 P2' _chemical_formula_weight 1054.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 14.2295(10) _cell_length_b 13.2351(10) _cell_length_c 24.1652(18) _cell_angle_alpha 90.00 _cell_angle_beta 101.6140(10) _cell_angle_gamma 90.00 _cell_volume 4457.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9302 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.0 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 1.384 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.732 _exptl_absorpt_correction_T_max 0.789 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _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 'Bruker SMART APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28489 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4750 _reflns_number_gt 4576 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_publication_material 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _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^)+(0.0200P)^2^+265.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4750 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.1718 _refine_ls_wR_factor_gt 0.1707 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 La1 La 0.0000 0.40489(4) 0.2500 0.01258(16) Uani 1 2 d S . . Cl1 Cl 0.06600(13) 0.56740(12) 0.18858(8) 0.0192(4) Uani 1 1 d . . . Cl2 Cl 0.0000 0.1961(2) 0.2500 0.0508(11) Uani 1 2 d S . . Cl3 Cl 0.35384(17) 0.3563(2) 0.03740(9) 0.0385(6) Uani 1 1 d . . . P1 P 0.26943(14) 0.36763(16) 0.31629(9) 0.0200(4) Uani 1 1 d . A . O1 O 0.1658(4) 0.3916(5) 0.2931(2) 0.0268(13) Uani 1 1 d . . . O2 O 0.4414(4) 0.6390(4) 0.3749(3) 0.0261(12) Uani 1 1 d . . . O3 O 0.3088(6) 0.1657(5) 0.4643(3) 0.0460(19) Uani 1 1 d . . . O4 O 0.0271(4) 0.3389(4) 0.1558(2) 0.0238(12) Uani 1 1 d . . . H4A H 0.0410 0.3702 0.1263 0.029 Uiso 1 1 d R . . H4B H 0.0289 0.2743 0.1474 0.029 Uiso 1 1 d R . . N1 N 0.3209(5) 0.2958(5) 0.2757(3) 0.0223(14) Uani 1 1 d . . . H1N H 0.3403 0.2364 0.2923 0.027 Uiso 1 1 d R . . N2 N 0.3317(5) 0.4728(5) 0.3252(3) 0.0199(13) Uani 1 1 d . . . N3 N 0.2783(5) 0.3070(7) 0.3758(3) 0.0343(19) Uani 1 1 d . . . C1 C 0.3292(5) 0.3150(6) 0.2202(3) 0.0194(15) Uani 1 1 d . . . C2 C 0.2791(6) 0.3928(7) 0.1875(4) 0.0251(17) Uani 1 1 d . . . H2A H 0.2403 0.4378 0.2038 0.030 Uiso 1 1 calc R . . C3 C 0.2860(6) 0.4041(7) 0.1319(4) 0.0278(17) Uani 1 1 d . . . H3A H 0.2500 0.4554 0.1095 0.033 Uiso 1 1 calc R . . C4 C 0.3451(6) 0.3411(7) 0.1083(3) 0.0246(17) Uani 1 1 d . . . C5 C 0.3956(6) 0.2640(7) 0.1389(4) 0.0252(17) Uani 1 1 d . . . H5A H 0.4351 0.2206 0.1222 0.030 Uiso 1 1 calc R . . C6 C 0.3878(5) 0.2509(6) 0.1952(4) 0.0234(16) Uani 1 1 d . . . H6A H 0.4225 0.1981 0.2168 0.028 Uiso 1 1 calc R . . C7 C 0.2858(6) 0.5696(6) 0.3348(4) 0.0260(17) Uani 1 1 d . . . H7A H 0.2209 0.5568 0.3422 0.031 Uiso 1 1 calc R . . H7B H 0.2791 0.6125 0.3006 0.031 Uiso 1 1 calc R . . C8 C 0.3465(6) 0.6233(7) 0.3847(4) 0.0290(18) Uani 1 1 d . . . H8A H 0.3171 0.6892 0.3905 0.035 Uiso 1 1 calc R . . H8B H 0.3496 0.5823 0.4193 0.035 Uiso 1 1 calc R . . C9 C 0.4873(5) 0.5456(6) 0.3657(4) 0.0242(17) Uani 1 1 d . . . H9A H 0.4962 0.5044 0.4006 0.029 Uiso 1 1 calc R . . H9B H 0.5515 0.5603 0.3578 0.029 Uiso 1 1 calc R . . C10 C 0.4294(5) 0.4847(6) 0.3166(3) 0.0199(15) Uani 1 1 d . . . H10A H 0.4289 0.5203 0.2805 0.024 Uiso 1 1 calc R . . H10B H 0.4592 0.4176 0.3147 0.024 Uiso 1 1 calc R . . C11 C 0.3731(12) 0.2801(15) 0.4095(8) 0.022(4) Uani 0.50 1 d P A 1 H11A H 0.4187 0.3369 0.4105 0.026 Uiso 0.50 1 calc PR A 1 H11B H 0.3993 0.2201 0.3935 0.026 Uiso 0.50 1 calc PR A 1 C12 C 0.3559(11) 0.2573(13) 0.4691(7) 0.022(3) Uani 0.50 1 d P A 1 H12A H 0.4175 0.2529 0.4966 0.027 Uiso 0.50 1 calc PR A 1 H12B H 0.3160 0.3107 0.4816 0.027 Uiso 0.50 1 calc PR A 1 C13 C 0.2048(11) 0.1868(12) 0.4322(7) 0.020(3) Uani 0.50 1 d P A 1 H13A H 0.1631 0.1274 0.4337 0.024 Uiso 0.50 1 calc PR A 1 H13B H 0.1773 0.2459 0.4483 0.024 Uiso 0.50 1 calc PR A 1 C14 C 0.2155(11) 0.2076(13) 0.3721(7) 0.020(3) Uani 0.50 1 d P A 1 H14A H 0.1520 0.2181 0.3472 0.024 Uiso 0.50 1 calc PR A 1 H14B H 0.2482 0.1507 0.3573 0.024 Uiso 0.50 1 calc PR A 1 C11' C 0.3622(12) 0.3247(15) 0.4267(7) 0.021(3) Uani 0.50 1 d P A 2 H11C H 0.4142 0.3637 0.4149 0.025 Uiso 0.50 1 calc PR A 2 H11D H 0.3399 0.3620 0.4571 0.025 Uiso 0.50 1 calc PR A 2 C12' C 0.3967(12) 0.2208(13) 0.4464(8) 0.027(4) Uani 0.50 1 d P A 2 H12C H 0.4514 0.2254 0.4789 0.032 Uiso 0.50 1 calc PR A 2 H12D H 0.4177 0.1832 0.4156 0.032 Uiso 0.50 1 calc PR A 2 C13' C 0.2470(14) 0.1510(14) 0.4118(7) 0.029(4) Uani 0.50 1 d P A 2 H13C H 0.1966 0.1012 0.4153 0.035 Uiso 0.50 1 calc PR A 2 H13D H 0.2834 0.1254 0.3838 0.035 Uiso 0.50 1 calc PR A 2 C14' C 0.2016(13) 0.2536(15) 0.3929(7) 0.025(3) Uani 0.50 1 d P A 2 H14C H 0.1462 0.2458 0.3610 0.030 Uiso 0.50 1 calc PR A 2 H14D H 0.1802 0.2885 0.4244 0.030 Uiso 0.50 1 calc PR A 2 N4 N 0.0718(6) 0.4001(7) 0.0458(3) 0.0403(19) Uani 1 1 d . . . C15 C 0.0956(6) 0.4285(6) 0.0059(4) 0.0289(18) Uani 1 1 d . . . C16 C 0.1232(7) 0.4646(8) -0.0459(4) 0.034(2) Uani 1 1 d . . . H16A H 0.0680 0.4604 -0.0774 0.051 Uiso 1 1 calc R . . H16B H 0.1755 0.4227 -0.0541 0.051 Uiso 1 1 calc R . . H16C H 0.1447 0.5350 -0.0408 0.051 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 La1 0.0108(3) 0.0084(3) 0.0187(3) 0.000 0.00325(19) 0.000 Cl1 0.0239(9) 0.0083(7) 0.0269(9) 0.0023(6) 0.0087(7) -0.0005(6) Cl2 0.112(4) 0.0121(13) 0.0404(18) 0.000 0.044(2) 0.000 Cl3 0.0307(11) 0.0595(16) 0.0257(10) -0.0042(10) 0.0067(8) -0.0015(11) P1 0.0137(9) 0.0225(10) 0.0239(10) 0.0094(8) 0.0039(7) 0.0017(7) O1 0.018(3) 0.039(4) 0.024(3) 0.007(3) 0.005(2) 0.007(3) O2 0.027(3) 0.018(3) 0.034(3) -0.001(2) 0.009(2) 0.001(2) O3 0.059(5) 0.029(4) 0.040(4) 0.020(3) -0.016(3) -0.012(3) O4 0.038(3) 0.012(2) 0.024(3) -0.002(2) 0.014(2) 0.000(2) N1 0.018(3) 0.014(3) 0.034(4) 0.004(3) 0.002(3) -0.001(2) N2 0.016(3) 0.015(3) 0.029(3) 0.002(3) 0.006(3) 0.005(2) N3 0.015(3) 0.055(5) 0.029(4) 0.024(4) -0.002(3) -0.003(3) C1 0.013(3) 0.015(4) 0.029(4) -0.004(3) 0.001(3) -0.001(3) C2 0.019(4) 0.024(4) 0.033(4) 0.001(3) 0.006(3) 0.002(3) C3 0.021(4) 0.032(4) 0.030(4) 0.001(4) 0.004(3) 0.009(4) C4 0.021(4) 0.029(4) 0.024(4) -0.006(3) 0.004(3) -0.005(3) C5 0.018(4) 0.026(4) 0.031(4) -0.006(3) 0.003(3) -0.005(3) C6 0.015(4) 0.017(4) 0.037(4) 0.000(3) 0.002(3) 0.001(3) C7 0.025(4) 0.014(4) 0.039(5) -0.003(3) 0.006(3) 0.008(3) C8 0.032(5) 0.025(4) 0.033(5) -0.002(3) 0.014(4) 0.005(3) C9 0.013(3) 0.021(4) 0.038(5) 0.006(3) 0.003(3) 0.001(3) C10 0.016(4) 0.020(4) 0.026(4) 0.004(3) 0.009(3) -0.004(3) C11 0.013(7) 0.015(8) 0.037(10) 0.004(8) 0.006(7) 0.005(6) C12 0.013(7) 0.026(8) 0.024(8) 0.001(7) -0.004(6) -0.004(6) C13 0.011(7) 0.019(8) 0.028(8) 0.005(6) 0.001(6) -0.003(6) C14 0.020(8) 0.016(8) 0.023(8) 0.003(7) 0.004(6) 0.003(6) C11' 0.021(8) 0.019(9) 0.020(8) 0.008(7) 0.000(6) -0.002(7) C12' 0.024(8) 0.022(8) 0.036(9) 0.020(7) 0.010(7) 0.006(7) C13' 0.031(10) 0.027(9) 0.029(9) -0.005(7) 0.003(8) -0.017(8) C14' 0.029(9) 0.029(10) 0.016(8) 0.003(7) 0.007(7) -0.006(8) N4 0.041(5) 0.045(5) 0.035(4) 0.013(4) 0.009(4) 0.002(4) C15 0.029(4) 0.024(4) 0.033(5) -0.003(3) 0.007(4) 0.000(3) C16 0.029(5) 0.035(5) 0.038(5) -0.003(4) 0.008(4) -0.003(4) _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 La1 O1 2.386(5) . ? La1 O1 2.386(5) 2 ? La1 O4 2.540(5) 2 ? La1 O4 2.540(5) . ? La1 Cl2 2.763(3) . ? La1 Cl1 2.8762(17) 2 ? La1 Cl1 2.8762(17) . ? Cl3 C4 1.755(8) . ? P1 O1 1.503(6) . ? P1 N3 1.630(7) . ? P1 N2 1.641(7) . ? P1 N1 1.641(7) . ? O2 C8 1.432(10) . ? O2 C9 1.435(9) . ? O3 C12 1.379(17) . ? O3 C13' 1.405(18) . ? O3 C13 1.551(16) . ? O3 C12' 1.581(18) . ? O4 H4A 0.8799 . ? O4 H4B 0.8800 . ? N1 C1 1.391(11) . ? N1 H1N 0.9000 . ? N2 C10 1.456(9) . ? N2 C7 1.476(9) . ? N3 C14' 1.429(18) . ? N3 C11 1.472(17) . ? N3 C11' 1.549(18) . ? N3 C14 1.582(18) . ? C1 C2 1.404(11) . ? C1 C6 1.409(11) . ? C2 C3 1.375(12) . ? C2 H2A 0.9500 . ? C3 C4 1.386(12) . ? C3 H3A 0.9500 . ? C4 C5 1.375(12) . ? C5 C6 1.396(12) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.514(12) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.530(11) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.54(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.51(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C11' C12' 1.51(2) . ? C11' H11C 0.9900 . ? C11' H11D 0.9900 . ? C12' H12C 0.9900 . ? C12' H12D 0.9900 . ? C13' C14' 1.53(3) . ? C13' H13C 0.9900 . ? C13' H13D 0.9900 . ? C14' H14C 0.9900 . ? C14' H14D 0.9900 . ? N4 C15 1.149(12) . ? C15 C16 1.465(13) . ? 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 O1 La1 O1 171.6(3) . 2 ? O1 La1 O4 84.18(19) . 2 ? O1 La1 O4 92.92(19) 2 2 ? O1 La1 O4 92.92(19) . . ? O1 La1 O4 84.18(19) 2 . ? O4 La1 O4 139.7(2) 2 . ? O1 La1 Cl2 85.78(16) . . ? O1 La1 Cl2 85.78(16) 2 . ? O4 La1 Cl2 69.87(12) 2 . ? O4 La1 Cl2 69.87(12) . . ? O1 La1 Cl1 103.10(16) . 2 ? O1 La1 Cl1 83.30(15) 2 2 ? O4 La1 Cl1 70.75(13) 2 2 ? O4 La1 Cl1 147.59(13) . 2 ? Cl2 La1 Cl1 138.40(4) . 2 ? O1 La1 Cl1 83.30(15) . . ? O1 La1 Cl1 103.10(16) 2 . ? O4 La1 Cl1 147.59(13) 2 . ? O4 La1 Cl1 70.75(13) . . ? Cl2 La1 Cl1 138.40(4) . . ? Cl1 La1 Cl1 83.20(7) 2 . ? O1 P1 N3 109.2(3) . . ? O1 P1 N2 109.4(4) . . ? N3 P1 N2 110.9(4) . . ? O1 P1 N1 115.0(3) . . ? N3 P1 N1 106.2(4) . . ? N2 P1 N1 106.0(3) . . ? P1 O1 La1 171.3(4) . . ? C8 O2 C9 112.0(6) . . ? C12 O3 C13 106.4(10) . . ? C13' O3 C12' 101.7(11) . . ? La1 O4 H4A 131.5 . . ? La1 O4 H4B 123.8 . . ? H4A O4 H4B 104.5 . . ? C1 N1 P1 127.2(6) . . ? C1 N1 H1N 120.7 . . ? P1 N1 H1N 111.8 . . ? C10 N2 C7 113.2(6) . . ? C10 N2 P1 125.4(5) . . ? C7 N2 P1 120.8(5) . . ? C14' N3 C11' 111.0(10) . . ? C11 N3 C14 105.9(10) . . ? C14' N3 P1 124.8(8) . . ? C11 N3 P1 120.4(8) . . ? C11' N3 P1 122.4(8) . . ? C14 N3 P1 114.6(8) . . ? N1 C1 C2 123.0(7) . . ? N1 C1 C6 118.5(7) . . ? C2 C1 C6 118.5(8) . . ? C3 C2 C1 120.2(8) . . ? C3 C2 H2A 119.9 . . ? C1 C2 H2A 119.9 . . ? C2 C3 C4 120.3(8) . . ? C2 C3 H3A 119.9 . . ? C4 C3 H3A 119.9 . . ? C5 C4 C3 121.4(8) . . ? C5 C4 Cl3 118.5(7) . . ? C3 C4 Cl3 120.0(7) . . ? C4 C5 C6 118.7(8) . . ? C4 C5 H5A 120.7 . . ? C6 C5 H5A 120.7 . . ? C5 C6 C1 120.9(8) . . ? C5 C6 H6A 119.5 . . ? C1 C6 H6A 119.5 . . ? N2 C7 C8 109.4(7) . . ? N2 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N2 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? O2 C8 C7 110.0(7) . . ? O2 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? O2 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? O2 C9 C10 112.5(6) . . ? O2 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? O2 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? N2 C10 C9 109.0(6) . . ? N2 C10 H10A 109.9 . . ? C9 C10 H10A 109.9 . . ? N2 C10 H10B 109.9 . . ? C9 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? N3 C11 C12 105.3(12) . . ? N3 C11 H11A 110.7 . . ? C12 C11 H11A 110.7 . . ? N3 C11 H11B 110.7 . . ? C12 C11 H11B 110.7 . . ? H11A C11 H11B 108.8 . . ? O3 C12 C11 105.1(13) . . ? O3 C12 H12A 110.7 . . ? C11 C12 H12A 110.7 . . ? O3 C12 H12B 110.7 . . ? C11 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C14 C13 O3 104.0(12) . . ? C14 C13 H13A 110.9 . . ? O3 C13 H13A 110.9 . . ? C14 C13 H13B 110.9 . . ? O3 C13 H13B 110.9 . . ? H13A C13 H13B 109.0 . . ? C13 C14 N3 105.2(13) . . ? C13 C14 H14A 110.7 . . ? N3 C14 H14A 110.7 . . ? C13 C14 H14B 110.7 . . ? N3 C14 H14B 110.7 . . ? H14A C14 H14B 108.8 . . ? C12' C11' N3 105.3(14) . . ? C12' C11' H11C 110.7 . . ? N3 C11' H11C 110.7 . . ? C12' C11' H11D 110.7 . . ? N3 C11' H11D 110.7 . . ? H11C C11' H11D 108.8 . . ? C11' C12' O3 106.4(12) . . ? C11' C12' H12C 110.4 . . ? O3 C12' H12C 110.4 . . ? C11' C12' H12D 110.4 . . ? O3 C12' H12D 110.4 . . ? H12C C12' H12D 108.6 . . ? O3 C13' C14' 107.2(14) . . ? O3 C13' H13C 110.3 . . ? C14' C13' H13C 110.3 . . ? O3 C13' H13D 110.3 . . ? C14' C13' H13D 110.3 . . ? H13C C13' H13D 108.5 . . ? N3 C14' C13' 102.9(14) . . ? N3 C14' H14C 111.2 . . ? C13' C14' H14C 111.2 . . ? N3 C14' H14D 111.2 . . ? C13' C14' H14D 111.2 . . ? H14C C14' H14D 109.1 . . ? N4 C15 C16 178.5(10) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 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 O1 P1 N1 C1 57.7(7) . . . . ? N3 P1 N1 C1 178.5(6) . . . . ? N2 P1 N1 C1 -63.4(7) . . . . ? O1 P1 N2 C10 -144.4(6) . . . . ? N3 P1 N2 C10 95.0(7) . . . . ? N1 P1 N2 C10 -19.8(7) . . . . ? O1 P1 N2 C7 26.0(7) . . . . ? N3 P1 N2 C7 -94.6(7) . . . . ? N1 P1 N2 C7 150.6(6) . . . . ? O1 P1 N3 C14' 20.9(14) . . . . ? N2 P1 N3 C14' 141.7(13) . . . . ? N1 P1 N3 C14' -103.6(13) . . . . ? O1 P1 N3 C11 -176.0(11) . . . . ? N2 P1 N3 C11 -55.3(12) . . . . ? N1 P1 N3 C11 59.5(12) . . . . ? O1 P1 N3 C11' -142.2(11) . . . . ? N2 P1 N3 C11' -21.5(12) . . . . ? N1 P1 N3 C11' 93.3(12) . . . . ? O1 P1 N3 C14 55.8(9) . . . . ? N2 P1 N3 C14 176.5(8) . . . . ? N1 P1 N3 C14 -68.7(9) . . . . ? P1 N1 C1 C2 -11.4(11) . . . . ? P1 N1 C1 C6 171.1(6) . . . . ? N1 C1 C2 C3 -176.1(8) . . . . ? C6 C1 C2 C3 1.4(12) . . . . ? C1 C2 C3 C4 -2.3(13) . . . . ? C2 C3 C4 C5 2.2(13) . . . . ? C2 C3 C4 Cl3 -179.8(7) . . . . ? C3 C4 C5 C6 -1.1(12) . . . . ? Cl3 C4 C5 C6 -179.2(6) . . . . ? C4 C5 C6 C1 0.2(12) . . . . ? N1 C1 C6 C5 177.3(7) . . . . ? C2 C1 C6 C5 -0.3(11) . . . . ? C10 N2 C7 C8 -56.7(9) . . . . ? P1 N2 C7 C8 131.8(6) . . . . ? C9 O2 C8 C7 -58.8(9) . . . . ? N2 C7 C8 O2 57.6(9) . . . . ? C8 O2 C9 C10 56.9(9) . . . . ? C7 N2 C10 C9 53.2(8) . . . . ? P1 N2 C10 C9 -135.7(6) . . . . ? O2 C9 C10 N2 -52.5(8) . . . . ? C14' N3 C11 C12 -33.1(19) . . . . ? C11' N3 C11 C12 59(2) . . . . ? C14 N3 C11 C12 -66.0(16) . . . . ? P1 N3 C11 C12 161.9(10) . . . . ? C13' O3 C12 C11 -33.7(17) . . . . ? C13 O3 C12 C11 -73.6(14) . . . . ? C12' O3 C12 C11 45.0(14) . . . . ? N3 C11 C12 O3 72.6(16) . . . . ? C12 O3 C13 C14 71.9(15) . . . . ? C13' O3 C13 C14 -35.9(14) . . . . ? C12' O3 C13 C14 32.2(17) . . . . ? O3 C13 C14 N3 -63.9(13) . . . . ? C14' N3 C14 C13 -42.6(17) . . . . ? C11 N3 C14 C13 65.3(15) . . . . ? C11' N3 C14 C13 38.2(17) . . . . ? P1 N3 C14 C13 -159.5(9) . . . . ? C14' N3 C11' C12' 62.3(17) . . . . ? C11 N3 C11' C12' -37.4(18) . . . . ? C14 N3 C11' C12' 28.5(18) . . . . ? P1 N3 C11' C12' -132.5(11) . . . . ? N3 C11' C12' O3 -60.7(16) . . . . ? C12 O3 C12' C11' -43.6(14) . . . . ? C13' O3 C12' C11' 70.0(16) . . . . ? C13 O3 C12' C11' 34.3(18) . . . . ? C12 O3 C13' C14' -36.3(18) . . . . ? C13 O3 C13' C14' 50.1(15) . . . . ? C12' O3 C13' C14' -75.1(15) . . . . ? C11 N3 C14' C13' -33.3(18) . . . . ? C11' N3 C14' C13' -64.3(17) . . . . ? C14 N3 C14' C13' 50.0(17) . . . . ? P1 N3 C14' C13' 130.9(11) . . . . ? O3 C13' C14' N3 74.4(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1N Cl1 4_545 0.90 2.60 3.452(7) 159 ? O4 H4A N4 . 0.88 2.12 2.968(9) 163 ? O4 H4B O2 4_545 0.88 1.94 2.808(8) 168 ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 1.452 _refine_diff_density_min -1.534 _refine_diff_density_rms 0.087 _publ_section_references ; Bruker (2001). SAINTPlus, v. 6.2. Data Reduction and Correction Program, Bruker AXS, Madison, Wisconsin, USA. Bruker (2005). APEX2 software package, v. 1.27. Bruker Molecular Analysis Research Tool, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2003). SADABS, v. 2.03, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2001). SHELXTL, v. 6.12, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; The H atoms of the NH-group, the coordinated water molecule and the solvate acetonitrile molecule were located in the difference Fourier map and refined in rigid model with fixed thermal parameters. The other H(C) atoms were placed in calculated positions and refined in riding model with fixed thermal parameters (Uiso(H) = 1.2Ueq(C)), where Ueq(C) are the equivalent thermal parameters of the carbon atoms, respectively, to which corresponding H atoms are bonded. There is a high positive residual density of 1.45 e\A^-3^ near the La1 (0.97 A) center due to considerable absorption effects, which could not be completely corrected. ; # end Validation Reply Form data_CeClPA #TrackingRef '- Stractures.CIF' _database_code_depnum_ccdc_archive 'CCDC 678076' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H51.60 Ce Cl5 N6 O8.80 P2' _chemical_formula_sum 'C30 H51.60 Ce Cl5 N6 O8.80 P2' _chemical_formula_weight 1016.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 14.3165(4) _cell_length_b 13.0127(4) _cell_length_c 23.8088(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.5550(10) _cell_angle_gamma 90.00 _cell_volume 4293.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 745 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2068 _exptl_absorpt_coefficient_mu 1.499 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.707 _exptl_absorpt_correction_T_max 0.864 _exptl_absorpt_process_details 'APEX2 (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25803 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 29.00 _reflns_number_total 5707 _reflns_number_gt 5324 _reflns_threshold_expression I>2/s(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'APEX2 (Bruker, 2005)' _computing_data_reduction 'APEX2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _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^)+(0.0650P)^2^+2.2000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5707 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0876 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.005 _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 Ce1 Ce 0.0000 0.191659(12) 0.2500 0.00947(6) Uani 1 2 d S . . P1 P 0.22203(4) 0.14651(4) 0.18901(2) 0.01096(11) Uani 1 1 d . . . O1 O 0.13551(11) 0.17061(13) 0.21075(7) 0.0153(3) Uani 1 1 d . A . N1 N 0.30530(14) 0.07793(14) 0.23387(8) 0.0145(4) Uani 1 1 d . A . H1N H 0.3225 0.0226 0.2216 0.017 Uiso 1 1 d R . . N2 N 0.27342(13) 0.25215(14) 0.17562(8) 0.0140(4) Uani 1 1 d . A . N3 N 0.18942(13) 0.07750(14) 0.12975(8) 0.0134(4) Uani 1 1 d . A . O2 O 0.34496(13) 0.41978(13) 0.12251(8) 0.0192(3) Uani 1 1 d . . . O3 O 0.13266(14) -0.04913(16) 0.03080(8) 0.0272(4) Uani 1 1 d . . . C1 C 0.35363(15) 0.10092(16) 0.29199(10) 0.0128(4) Uani 1 1 d . . . C2 C 0.43176(16) 0.03942(18) 0.31898(10) 0.0172(4) Uani 1 1 d . A . H2A H 0.4526 -0.0137 0.2976 0.021 Uiso 1 1 calc R . . C3 C 0.47941(17) 0.0551(2) 0.37680(11) 0.0215(5) Uani 1 1 d . . . H3A H 0.5318 0.0122 0.3953 0.026 Uiso 1 1 calc R A . C4 C 0.44950(18) 0.1340(2) 0.40695(11) 0.0221(5) Uani 1 1 d . A . C5 C 0.37233(19) 0.19684(18) 0.38060(11) 0.0208(5) Uani 1 1 d . . . H5A H 0.3529 0.2510 0.4019 0.025 Uiso 1 1 calc R A . C6 C 0.32401(17) 0.18006(18) 0.32317(11) 0.0172(4) Uani 1 1 d . A . H6A H 0.2708 0.2223 0.3051 0.021 Uiso 1 1 calc R . . C7 C 0.22031(18) 0.34965(18) 0.16423(11) 0.0194(5) Uani 1 1 d . . . H7A H 0.2388 0.3945 0.1988 0.023 Uiso 1 1 calc R A . H7B H 0.1501 0.3363 0.1560 0.023 Uiso 1 1 calc R . . C8 C 0.24340(18) 0.40289(19) 0.11265(11) 0.0207(5) Uani 1 1 d . A . H8A H 0.2204 0.3601 0.0775 0.025 Uiso 1 1 calc R . . H8B H 0.2092 0.4696 0.1059 0.025 Uiso 1 1 calc R . . C9 C 0.39766(18) 0.32554(19) 0.13333(12) 0.0203(5) Uani 1 1 d . A . H9A H 0.4676 0.3406 0.1414 0.024 Uiso 1 1 calc R . . H9B H 0.3801 0.2821 0.0981 0.024 Uiso 1 1 calc R . . C10 C 0.37802(16) 0.26667(18) 0.18390(11) 0.0169(4) Uani 1 1 d . . . H10A H 0.4103 0.1989 0.1871 0.020 Uiso 1 1 calc R A . H10B H 0.4046 0.3049 0.2204 0.020 Uiso 1 1 calc R . . C11 C 0.25249(17) 0.06315(19) 0.09041(10) 0.0183(5) Uani 1 1 d . . . H11A H 0.2977 0.0056 0.1042 0.022 Uiso 1 1 calc R A . H11B H 0.2908 0.1262 0.0895 0.022 Uiso 1 1 calc R . . C12 C 0.1905(2) 0.0398(2) 0.03012(11) 0.0284(6) Uani 1 1 d . A . H12A H 0.1482 0.0994 0.0157 0.034 Uiso 1 1 calc R . . H12B H 0.2324 0.0284 0.0034 0.034 Uiso 1 1 calc R . . C13 C 0.07001(17) -0.0335(2) 0.06843(10) 0.0216(5) Uani 1 1 d . A . H13A H 0.0291 -0.0951 0.0676 0.026 Uiso 1 1 calc R . . H13B H 0.0271 0.0257 0.0545 0.026 Uiso 1 1 calc R . . C14 C 0.12773(16) -0.01363(17) 0.13009(10) 0.0153(4) Uani 1 1 d . . . H14A H 0.0837 -0.0010 0.1554 0.018 Uiso 1 1 calc R A . H14B H 0.1682 -0.0741 0.1452 0.018 Uiso 1 1 calc R . . Cl3 Cl 0.51018(6) 0.15643(6) 0.47938(3) 0.03734(18) Uani 1 1 d . . . Cl1 Cl 0.11310(4) 0.35796(4) 0.30705(2) 0.01571(11) Uani 1 1 d . A . Cl2 Cl 0.0000 -0.02089(6) 0.2500 0.01995(16) Uani 1 2 d S A . O1S O 0.0917(8) 0.1216(8) 0.3447(5) 0.0156(17) Uani 0.60 1 d P A 1 H1S H 0.1029 0.0555 0.3488 0.045 Uiso 0.60 1 d P B 1 C1S C 0.1220(4) 0.1669(4) 0.4049(2) 0.0338(11) Uani 0.60 1 d P A 1 H1SA H 0.1410 0.1116 0.4334 0.051 Uiso 0.60 1 calc PR A 1 H1SB H 0.0679 0.2053 0.4130 0.051 Uiso 0.60 1 calc PR A 1 H1SC H 0.1767 0.2134 0.4074 0.051 Uiso 0.60 1 calc PR A 1 O1W O 0.0919(14) 0.1296(15) 0.3504(8) 0.021(4) Uiso 0.40 1 d P A 2 H1WA H 0.1029 0.0555 0.3488 0.045 Uiso 0.40 1 d P C 2 H1WB H 0.1115 0.1536 0.3810 0.054 Uiso 0.40 1 d PR C 2 O2S O 0.1307(5) 0.2020(5) 0.4498(3) 0.0500(16) Uiso 0.40 1 d P D 2 H2S H 0.0709 0.2253 0.4482 0.060 Uiso 0.40 1 d PR D 2 C2S C 0.1944(6) 0.2843(7) 0.4663(4) 0.0409(18) Uiso 0.40 1 d P D 2 H2SA H 0.1748 0.3251 0.4960 0.049 Uiso 0.40 1 calc PR D 2 H2SB H 0.1934 0.3275 0.4325 0.049 Uiso 0.40 1 calc PR D 2 H2SC H 0.2599 0.2579 0.4822 0.049 Uiso 0.40 1 calc PR D 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ce1 0.00812(9) 0.00750(9) 0.01337(9) 0.000 0.00379(6) 0.000 P1 0.0095(2) 0.0092(2) 0.0151(3) -0.00142(19) 0.0049(2) -0.00042(18) O1 0.0127(7) 0.0158(7) 0.0194(8) -0.0030(6) 0.0079(6) -0.0006(6) N1 0.0163(9) 0.0088(8) 0.0184(9) -0.0015(7) 0.0045(7) 0.0030(7) N2 0.0111(8) 0.0101(8) 0.0222(9) 0.0014(7) 0.0071(7) 0.0013(7) N3 0.0119(8) 0.0140(9) 0.0161(9) -0.0041(7) 0.0065(7) -0.0038(7) O2 0.0200(8) 0.0148(8) 0.0229(9) 0.0026(6) 0.0058(7) -0.0024(6) O3 0.0323(10) 0.0311(10) 0.0199(9) -0.0098(8) 0.0096(8) -0.0108(8) C1 0.0109(9) 0.0092(9) 0.0178(10) 0.0011(8) 0.0026(8) -0.0018(7) C2 0.0125(10) 0.0131(10) 0.0270(12) 0.0021(9) 0.0070(9) 0.0010(8) C3 0.0122(10) 0.0195(11) 0.0308(13) 0.0065(10) 0.0014(9) -0.0013(9) C4 0.0205(11) 0.0234(12) 0.0192(11) 0.0013(9) -0.0014(9) -0.0056(10) C5 0.0240(12) 0.0155(11) 0.0220(12) -0.0007(9) 0.0039(10) -0.0015(9) C6 0.0152(10) 0.0153(11) 0.0202(11) -0.0006(8) 0.0027(9) 0.0003(8) C7 0.0201(11) 0.0130(10) 0.0287(12) 0.0057(9) 0.0128(10) 0.0060(9) C8 0.0192(11) 0.0185(11) 0.0242(12) 0.0061(9) 0.0051(9) -0.0007(9) C9 0.0204(11) 0.0144(10) 0.0295(13) -0.0002(9) 0.0123(10) -0.0021(9) C10 0.0110(9) 0.0136(10) 0.0264(12) 0.0003(9) 0.0050(8) -0.0029(8) C11 0.0189(11) 0.0212(11) 0.0175(11) -0.0050(9) 0.0097(9) -0.0038(9) C12 0.0337(14) 0.0357(15) 0.0178(11) -0.0015(11) 0.0103(10) -0.0132(12) C13 0.0172(11) 0.0288(13) 0.0174(11) -0.0051(10) 0.0018(9) -0.0060(10) C14 0.0169(10) 0.0137(10) 0.0163(10) -0.0028(8) 0.0061(8) -0.0059(8) Cl3 0.0424(4) 0.0373(4) 0.0229(3) -0.0003(3) -0.0093(3) -0.0058(3) Cl1 0.0145(2) 0.0099(2) 0.0213(3) -0.00117(19) 0.0017(2) -0.00175(18) Cl2 0.0271(4) 0.0093(3) 0.0219(4) 0.000 0.0032(3) 0.000 O1S 0.025(3) 0.005(2) 0.011(3) -0.0016(18) -0.0053(17) -0.0001(15) C1S 0.059(3) 0.025(2) 0.017(2) -0.0006(17) 0.008(2) -0.007(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 Ce1 O1 2.3714(16) . ? Ce1 O1 2.3714(16) 2 ? Ce1 O1S 2.480(11) 2 ? Ce1 O1S 2.480(11) . ? Ce1 O1W 2.55(2) 2 ? Ce1 O1W 2.55(2) . ? Ce1 Cl2 2.7658(8) . ? Ce1 Cl1 2.8363(5) . ? Ce1 Cl1 2.8363(5) 2 ? P1 O1 1.4909(16) . ? P1 N2 1.6281(19) . ? P1 N3 1.6385(19) . ? P1 N1 1.649(2) . ? N1 C1 1.415(3) . ? N1 H1N 0.8368 . ? N2 C7 1.469(3) . ? N2 C10 1.473(3) . ? N3 C11 1.467(3) . ? N3 C14 1.480(3) . ? O2 C9 1.429(3) . ? O2 C8 1.430(3) . ? O3 C12 1.425(3) . ? O3 C13 1.433(3) . ? C1 C2 1.394(3) . ? C1 C6 1.396(3) . ? C2 C3 1.389(4) . ? C2 H2A 0.9500 . ? C3 C4 1.381(4) . ? C3 H3A 0.9500 . ? C4 C5 1.391(4) . ? C4 Cl3 1.750(3) . ? C5 C6 1.386(3) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.517(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.512(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.517(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.515(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? O1S C1S 1.508(12) . ? O1S H1S 0.8760 . ? O1S H1WA 0.8760 . ? O1S H1WB 0.9365 . ? C1S H1SA 0.9800 . ? C1S H1SB 0.9800 . ? C1S H1SC 0.9800 . ? C1S H1WB 0.5766 . ? O1W H1S 0.9798 . ? O1W H1WA 0.9798 . ? O1W H1WB 0.7780 . ? O2S C2S 1.398(11) . ? O2S H2S 0.9000 . ? C2S H2SA 0.9800 . ? C2S H2SB 0.9800 . ? C2S H2SC 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 O1 Ce1 O1 166.74(8) . 2 ? O1 Ce1 O1S 84.1(3) . 2 ? O1 Ce1 O1S 91.0(3) 2 2 ? O1 Ce1 O1S 91.0(3) . . ? O1 Ce1 O1S 84.1(3) 2 . ? O1S Ce1 O1S 136.9(5) 2 . ? O1 Ce1 O1W 82.8(5) . 2 ? O1 Ce1 O1W 93.0(5) 2 2 ? O1S Ce1 O1W 3.5(6) 2 2 ? O1S Ce1 O1W 140.0(2) . 2 ? O1 Ce1 O1W 93.0(4) . . ? O1 Ce1 O1W 82.8(5) 2 . ? O1S Ce1 O1W 140.0(2) 2 . ? O1S Ce1 O1W 3.5(6) . . ? O1W Ce1 O1W 143.1(8) 2 . ? O1 Ce1 Cl2 83.37(4) . . ? O1 Ce1 Cl2 83.37(4) 2 . ? O1S Ce1 Cl2 68.4(2) 2 . ? O1S Ce1 Cl2 68.4(2) . . ? O1W Ce1 Cl2 71.6(4) 2 . ? O1W Ce1 Cl2 71.6(4) . . ? O1 Ce1 Cl1 81.47(4) . . ? O1 Ce1 Cl1 108.94(4) 2 . ? O1S Ce1 Cl1 145.5(3) 2 . ? O1S Ce1 Cl1 74.7(2) . . ? O1W Ce1 Cl1 142.0(4) 2 . ? O1W Ce1 Cl1 72.2(4) . . ? Cl2 Ce1 Cl1 139.727(11) . . ? O1 Ce1 Cl1 108.94(4) . 2 ? O1 Ce1 Cl1 81.47(4) 2 2 ? O1S Ce1 Cl1 74.7(2) 2 2 ? O1S Ce1 Cl1 145.5(3) . 2 ? O1W Ce1 Cl1 72.2(4) 2 2 ? O1W Ce1 Cl1 142.0(4) . 2 ? Cl2 Ce1 Cl1 139.727(11) . 2 ? Cl1 Ce1 Cl1 80.55(2) . 2 ? O1 P1 N2 110.25(10) . . ? O1 P1 N3 109.42(10) . . ? N2 P1 N3 109.82(10) . . ? O1 P1 N1 114.68(10) . . ? N2 P1 N1 107.17(10) . . ? N3 P1 N1 105.33(10) . . ? P1 O1 Ce1 173.97(11) . . ? C1 N1 P1 127.98(15) . . ? C1 N1 H1N 114.2 . . ? P1 N1 H1N 117.8 . . ? C7 N2 C10 112.07(18) . . ? C7 N2 P1 121.81(15) . . ? C10 N2 P1 125.19(15) . . ? C11 N3 C14 111.44(18) . . ? C11 N3 P1 122.12(15) . . ? C14 N3 P1 118.41(15) . . ? C9 O2 C8 111.51(18) . . ? C12 O3 C13 110.4(2) . . ? C2 C1 C6 119.6(2) . . ? C2 C1 N1 117.9(2) . . ? C6 C1 N1 122.5(2) . . ? C3 C2 C1 120.6(2) . . ? C3 C2 H2A 119.7 . . ? C1 C2 H2A 119.7 . . ? C4 C3 C2 119.0(2) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 121.2(2) . . ? C3 C4 Cl3 119.6(2) . . ? C5 C4 Cl3 119.2(2) . . ? C6 C5 C4 119.7(2) . . ? C6 C5 H5A 120.2 . . ? C4 C5 H5A 120.2 . . ? C5 C6 C1 119.9(2) . . ? C5 C6 H6A 120.1 . . ? C1 C6 H6A 120.1 . . ? N2 C7 C8 109.63(19) . . ? N2 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? N2 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? O2 C8 C7 110.9(2) . . ? O2 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.0 . . ? O2 C9 C10 112.5(2) . . ? O2 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? O2 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? N2 C10 C9 110.16(19) . . ? N2 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? N2 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? N3 C11 C12 108.8(2) . . ? N3 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? N3 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? O3 C12 C11 110.8(2) . . ? O3 C12 H12A 109.5 . . ? C11 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? O3 C13 C14 110.82(19) . . ? O3 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? O3 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? N3 C14 C13 108.21(19) . . ? N3 C14 H14A 110.1 . . ? C13 C14 H14A 110.1 . . ? N3 C14 H14B 110.1 . . ? C13 C14 H14B 110.1 . . ? H14A C14 H14B 108.4 . . ? C1S O1S Ce1 132.8(6) . . ? C1S O1S H1S 106.1 . . ? Ce1 O1S H1S 120.1 . . ? C1S O1S H1WA 106.1 . . ? Ce1 O1S H1WA 120.1 . . ? H1S O1S H1WA 0.0 . . ? C1S O1S H1WB 3.6 . . ? Ce1 O1S H1WB 130.1 . . ? H1S O1S H1WB 109.2 . . ? H1WA O1S H1WB 109.2 . . ? O1S C1S H1WB 5.9 . . ? H1SA C1S H1WB 114.7 . . ? H1SB C1S H1WB 109.0 . . ? H1SC C1S H1WB 104.6 . . ? Ce1 O1W H1S 109.0 . . ? Ce1 O1W H1WA 109.0 . . ? H1S O1W H1WA 0.0 . . ? Ce1 O1W H1WB 137.0 . . ? H1S O1W H1WB 114.0 . . ? H1WA O1W H1WB 114.0 . . ? C2S O2S H2S 107.5 . . ? O2S C2S H2SA 109.5 . . ? O2S C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? O2S C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 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 O1 Ce1 -156.2(10) . . . . ? N3 P1 O1 Ce1 82.9(10) . . . . ? N1 P1 O1 Ce1 -35.2(10) . . . . ? O1 Ce1 O1 P1 -23.7(10) 2 . . . ? O1S Ce1 O1 P1 -92.6(10) 2 . . . ? O1S Ce1 O1 P1 44.4(10) . . . . ? O1W Ce1 O1 P1 -95.9(11) 2 . . . ? O1W Ce1 O1 P1 47.3(11) . . . . ? Cl2 Ce1 O1 P1 -23.7(10) . . . . ? Cl1 Ce1 O1 P1 118.8(10) . . . . ? Cl1 Ce1 O1 P1 -164.3(10) 2 . . . ? O1 P1 N1 C1 -56.4(2) . . . . ? N2 P1 N1 C1 66.3(2) . . . . ? N3 P1 N1 C1 -176.77(18) . . . . ? O1 P1 N2 C7 -22.5(2) . . . . ? N3 P1 N2 C7 98.16(19) . . . . ? N1 P1 N2 C7 -147.92(18) . . . . ? O1 P1 N2 C10 145.60(18) . . . . ? N3 P1 N2 C10 -93.8(2) . . . . ? N1 P1 N2 C10 20.2(2) . . . . ? O1 P1 N3 C11 164.56(18) . . . . ? N2 P1 N3 C11 43.4(2) . . . . ? N1 P1 N3 C11 -71.7(2) . . . . ? O1 P1 N3 C14 -49.33(19) . . . . ? N2 P1 N3 C14 -170.47(16) . . . . ? N1 P1 N3 C14 74.43(18) . . . . ? P1 N1 C1 C2 -170.56(17) . . . . ? P1 N1 C1 C6 11.5(3) . . . . ? C6 C1 C2 C3 1.0(3) . . . . ? N1 C1 C2 C3 -177.0(2) . . . . ? C1 C2 C3 C4 -1.3(4) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? C2 C3 C4 Cl3 -178.74(18) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? Cl3 C4 C5 C6 179.7(2) . . . . ? C4 C5 C6 C1 -0.6(4) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? N1 C1 C6 C5 177.9(2) . . . . ? C10 N2 C7 C8 55.3(3) . . . . ? P1 N2 C7 C8 -135.24(19) . . . . ? C9 O2 C8 C7 58.3(3) . . . . ? N2 C7 C8 O2 -57.3(3) . . . . ? C8 O2 C9 C10 -56.7(3) . . . . ? C7 N2 C10 C9 -53.1(2) . . . . ? P1 N2 C10 C9 137.86(18) . . . . ? O2 C9 C10 N2 53.2(3) . . . . ? C14 N3 C11 C12 56.9(3) . . . . ? P1 N3 C11 C12 -154.88(18) . . . . ? C13 O3 C12 C11 60.3(3) . . . . ? N3 C11 C12 O3 -57.9(3) . . . . ? C12 O3 C13 C14 -60.7(3) . . . . ? C11 N3 C14 C13 -57.0(2) . . . . ? P1 N3 C14 C13 153.47(16) . . . . ? O3 C13 C14 N3 58.1(3) . . . . ? O1 Ce1 O1S C1S 117.5(9) . . . . ? O1 Ce1 O1S C1S -74.8(9) 2 . . . ? O1S Ce1 O1S C1S -160.0(10) 2 . . . ? O1W Ce1 O1S C1S -162.5(4) 2 . . . ? O1W Ce1 O1S C1S -7(11) . . . . ? Cl2 Ce1 O1S C1S -160.0(10) . . . . ? Cl1 Ce1 O1S C1S 36.6(9) . . . . ? Cl1 Ce1 O1S C1S -9.2(13) 2 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1N Cl1 4_545 0.837 2.495 3.329(2) 174.63 ? O1S H1S O2 4_545 0.876 1.972 2.824(11) 163.92 ? O1W H1WA O2 4_545 0.980 1.972 2.899(11) 156.97 ? O1W H1WA Cl2 1_555 0.980 2.637 3.113(9) 110.12 ? O1W H1WB O2S 1_555 0.780 1.706 2.476(9) 168.67 ? O2S H2S Cl3 7_556 0.900 2.770 3.466(7) 135.05 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.097 _refine_diff_density_min -0.813 _refine_diff_density_rms 0.087 _publ_section_references ; Bruker (2005). APEX2 softwarwe package, Bruker AXS Inc., 5465, East Cheryl Parkway, Madison, WI 5317. Sheldrick G.M. (1998). SHELXTL v. 5.10, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; The hydrogen atoms of OH and NH groups and water molecule were found in difference Fourier synthesis. The H(C) atom positions were calculated. All hydrogen atoms were refined in isotropic approximation in riding model with the Uiso(H) parameters equal to 1.2 Ueq(Ci), for methyl groups equal to 1.5 Ueq(Cii), where U(Ci) and U(Cii) are respectively the equivalent thermal parameters of the carbon atoms to which corresponding H atoms are bonded. ; # end Validation Reply Form data_CeFPA #TrackingRef '- Stractures.CIF' _database_code_depnum_ccdc_archive 'CCDC 678077' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H46 Ce Cl3 F2 N6 O8 P2' _chemical_formula_sum 'C28 H46 Ce Cl3 F2 N6 O8 P2' _chemical_formula_weight 941.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'F d d 2' _symmetry_space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 14.444(3) _cell_length_b 40.900(8) _cell_length_c 12.960(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7656(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 843 _cell_measurement_theta_min 2.03 _cell_measurement_theta_max 21.56 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.190 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3816 _exptl_absorpt_coefficient_mu 1.545 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.706 _exptl_absorpt_correction_T_max 0.860 _exptl_absorpt_process_details 'Apex2 (Bruker, 2005)' _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 'Bruker Apex 2 CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11602 _diffrn_reflns_av_R_equivalents 0.0606 _diffrn_reflns_av_sigmaI/netI 0.0667 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -50 _diffrn_reflns_limit_k_max 50 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3681 _reflns_number_gt 3387 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'APEX2 (Bruker, 2005)' _computing_data_reduction 'APEX2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _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^)+(0.0400P)^2^+60.0000P] 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 0.015(18) _refine_ls_number_reflns 3681 _refine_ls_number_parameters 227 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.0978 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 Ce1 Ce 0.0000 0.0000 0.95572(3) 0.01550(12) Uani 1 2 d S . . Cl1 Cl -0.08210(10) -0.03558(4) 1.12386(12) 0.0221(3) Uani 1 1 d . . . Cl2 Cl 0.0000 0.0000 0.74320(17) 0.0317(5) Uani 1 2 d S . . P1 P -0.23595(10) 0.04167(4) 0.91997(12) 0.0169(3) Uani 1 1 d . . . F1 F -0.4218(3) -0.10585(9) 0.9452(4) 0.0420(10) Uani 1 1 d . . . O1 O -0.1420(3) 0.02887(9) 0.9426(3) 0.0225(9) Uani 1 1 d . . . O2 O -0.3799(3) 0.07216(10) 1.2037(4) 0.0240(9) Uani 1 1 d . . . O3 O -0.2103(3) 0.13396(11) 0.7358(3) 0.0280(11) Uani 1 1 d . . . N1 N -0.3001(3) 0.01828(12) 0.8462(4) 0.0195(11) Uani 1 1 d . . . H1 H -0.3169 0.0261 0.7858 0.023 Uiso 1 1 calc R . . N2 N -0.2927(4) 0.04560(13) 1.0265(4) 0.0203(11) Uani 1 1 d . . . N3 N -0.2256(3) 0.07689(12) 0.8584(4) 0.0180(11) Uani 1 1 d . . . C1 C -0.3307(4) -0.01375(14) 0.8722(5) 0.0182(12) Uani 1 1 d . . . C2 C -0.4026(4) -0.02811(16) 0.8153(5) 0.0213(14) Uani 1 1 d . . . H2 H -0.4309 -0.0165 0.7602 0.026 Uiso 1 1 calc R . . C3 C -0.4318(5) -0.05900(16) 0.8395(6) 0.0249(14) Uani 1 1 d . . . H3 H -0.4799 -0.0691 0.8009 0.030 Uiso 1 1 calc R . . C4 C -0.3909(5) -0.07541(15) 0.9205(5) 0.0277(15) Uani 1 1 d . . . C5 C -0.3192(5) -0.06217(15) 0.9760(5) 0.0282(15) Uani 1 1 d . . . H5 H -0.2910 -0.0742 1.0302 0.034 Uiso 1 1 calc R . . C6 C -0.2886(4) -0.03110(14) 0.9520(6) 0.0220(12) Uani 1 1 d . . . H6 H -0.2390 -0.0216 0.9898 0.026 Uiso 1 1 calc R . . C7 C -0.2465(4) 0.04530(16) 1.1277(5) 0.0217(13) Uani 1 1 d . . . H7A H -0.1788 0.0472 1.1182 0.026 Uiso 1 1 calc R . . H7B H -0.2594 0.0243 1.1632 0.026 Uiso 1 1 calc R . . C8 C -0.2810(4) 0.07335(14) 1.1930(5) 0.0234(13) Uani 1 1 d . . . H8A H -0.2519 0.0723 1.2621 0.028 Uiso 1 1 calc R . . H8B H -0.2629 0.0943 1.1606 0.028 Uiso 1 1 calc R . . C9 C -0.4275(5) 0.07202(17) 1.1066(5) 0.0263(15) Uani 1 1 d . . . H9A H -0.4165 0.0930 1.0706 0.032 Uiso 1 1 calc R . . H9B H -0.4949 0.0699 1.1187 0.032 Uiso 1 1 calc R . . C10 C -0.3945(4) 0.04395(16) 1.0390(5) 0.0216(13) Uani 1 1 d . . . H10A H -0.4119 0.0229 1.0711 0.026 Uiso 1 1 calc R . . H10B H -0.4248 0.0453 0.9706 0.026 Uiso 1 1 calc R . . C11 C -0.3058(4) 0.09768(15) 0.8356(6) 0.0238(13) Uani 1 1 d . . . H11A H -0.3499 0.0968 0.8940 0.029 Uiso 1 1 calc R . . H11B H -0.3379 0.0894 0.7734 0.029 Uiso 1 1 calc R . . C12 C -0.2762(5) 0.13228(16) 0.8178(5) 0.0258(15) Uani 1 1 d . . . H12A H -0.3309 0.1458 0.8004 0.031 Uiso 1 1 calc R . . H12B H -0.2484 0.1412 0.8818 0.031 Uiso 1 1 calc R . . C13 C -0.1318(5) 0.11435(16) 0.7581(6) 0.0278(14) Uani 1 1 d . . . H13A H -0.1014 0.1227 0.8213 0.033 Uiso 1 1 calc R . . H13B H -0.0869 0.1162 0.7007 0.033 Uiso 1 1 calc R . . C14 C -0.1561(5) 0.07919(16) 0.7735(5) 0.0257(14) Uani 1 1 d . . . H14A H -0.1822 0.0700 0.7091 0.031 Uiso 1 1 calc R . . H14B H -0.1000 0.0665 0.7917 0.031 Uiso 1 1 calc R . . O1W O 0.0610(3) 0.05371(10) 0.8936(3) 0.0214(9) Uani 1 1 d . . . H1W H 0.0797 0.0595 0.8341 0.032 Uiso 1 1 d R . . H2W H 0.0548 0.0724 0.9215 0.032 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 Ce1 0.01502(19) 0.0195(2) 0.0119(2) 0.000 0.000 0.0013(2) Cl1 0.0236(8) 0.0271(7) 0.0154(7) 0.0005(6) 0.0010(6) -0.0027(6) Cl2 0.0547(16) 0.0287(11) 0.0116(10) 0.000 0.000 -0.0149(11) P1 0.0132(7) 0.0215(7) 0.0159(8) 0.0017(6) -0.0005(6) 0.0010(6) F1 0.056(3) 0.0249(19) 0.045(3) 0.003(2) 0.005(2) -0.0125(18) O1 0.018(2) 0.027(2) 0.022(2) 0.0017(19) 0.0002(19) 0.0059(16) O2 0.024(2) 0.034(2) 0.013(2) -0.002(2) 0.002(2) 0.0006(17) O3 0.035(3) 0.025(2) 0.024(3) 0.0066(18) 0.006(2) 0.0033(19) N1 0.018(3) 0.029(3) 0.012(2) 0.005(2) -0.003(2) 0.000(2) N2 0.021(3) 0.028(3) 0.011(3) 0.003(2) -0.005(2) 0.003(2) N3 0.016(3) 0.026(3) 0.013(3) 0.005(2) 0.002(2) 0.000(2) C1 0.019(3) 0.019(3) 0.016(3) -0.001(2) -0.002(2) 0.004(2) C2 0.020(3) 0.028(3) 0.016(3) -0.005(2) 0.006(2) 0.004(3) C3 0.021(3) 0.029(3) 0.025(4) -0.011(3) -0.004(3) -0.001(3) C4 0.034(4) 0.022(3) 0.027(4) -0.001(3) 0.010(3) -0.003(3) C5 0.039(4) 0.025(3) 0.021(4) 0.005(3) 0.003(3) 0.005(3) C6 0.024(3) 0.026(3) 0.016(3) 0.001(3) -0.011(3) 0.005(2) C7 0.022(3) 0.031(3) 0.013(3) 0.001(2) -0.001(3) 0.000(2) C8 0.024(3) 0.028(3) 0.018(3) -0.002(3) -0.007(3) 0.001(2) C9 0.023(3) 0.041(4) 0.014(3) -0.003(3) 0.000(3) 0.006(3) C10 0.017(3) 0.032(4) 0.015(3) 0.001(3) 0.005(3) -0.002(3) C11 0.016(3) 0.030(3) 0.026(3) 0.000(3) 0.000(3) 0.004(3) C12 0.031(4) 0.028(3) 0.019(3) 0.002(3) 0.011(3) 0.006(3) C13 0.023(3) 0.034(4) 0.026(3) 0.006(3) 0.010(3) 0.001(3) C14 0.027(4) 0.031(3) 0.019(3) 0.003(3) 0.009(3) 0.008(3) O1W 0.028(2) 0.027(2) 0.010(2) 0.0011(17) 0.0047(18) -0.0021(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ce1 O1 2.373(4) 2 ? Ce1 O1 2.373(4) . ? Ce1 O1W 2.500(4) . ? Ce1 O1W 2.500(4) 2 ? Ce1 Cl2 2.754(2) . ? Ce1 Cl1 2.8762(16) 2 ? Ce1 Cl1 2.8762(16) . ? P1 O1 1.484(4) . ? P1 N2 1.613(5) . ? P1 N1 1.640(5) . ? P1 N3 1.654(5) . ? F1 C4 1.360(7) . ? O2 C9 1.434(8) . ? O2 C8 1.436(7) . ? O3 C13 1.419(8) . ? O3 C12 1.429(8) . ? N1 C1 1.423(7) . ? N1 H1 0.8800 . ? N2 C7 1.472(8) . ? N2 C10 1.481(8) . ? N3 C11 1.468(8) . ? N3 C14 1.492(8) . ? C1 C6 1.395(9) . ? C1 C2 1.403(8) . ? C2 C3 1.369(9) . ? C2 H2 0.9500 . ? C3 C4 1.379(10) . ? C3 H3 0.9500 . ? C4 C5 1.373(10) . ? C5 C6 1.381(9) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.510(9) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.520(9) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.496(9) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.493(9) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? O1W H1W 0.8501 . ? O1W H2W 0.8501 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ce1 O1 171.8(2) 2 . ? O1 Ce1 O1W 96.30(14) 2 . ? O1 Ce1 O1W 81.03(14) . . ? O1 Ce1 O1W 81.03(14) 2 2 ? O1 Ce1 O1W 96.30(14) . 2 ? O1W Ce1 O1W 142.43(19) . 2 ? O1 Ce1 Cl2 85.90(11) 2 . ? O1 Ce1 Cl2 85.90(11) . . ? O1W Ce1 Cl2 71.21(9) . . ? O1W Ce1 Cl2 71.21(9) 2 . ? O1 Ce1 Cl1 87.11(11) 2 2 ? O1 Ce1 Cl1 99.14(11) . 2 ? O1W Ce1 Cl1 69.77(10) . 2 ? O1W Ce1 Cl1 146.49(10) 2 2 ? Cl2 Ce1 Cl1 139.26(3) . 2 ? O1 Ce1 Cl1 99.14(11) 2 . ? O1 Ce1 Cl1 87.11(11) . . ? O1W Ce1 Cl1 146.49(10) . . ? O1W Ce1 Cl1 69.77(10) 2 . ? Cl2 Ce1 Cl1 139.26(3) . . ? Cl1 Ce1 Cl1 81.48(6) 2 . ? O1 P1 N2 109.3(3) . . ? O1 P1 N1 115.2(3) . . ? N2 P1 N1 105.7(3) . . ? O1 P1 N3 108.7(2) . . ? N2 P1 N3 111.9(3) . . ? N1 P1 N3 106.1(3) . . ? P1 O1 Ce1 168.6(3) . . ? C9 O2 C8 113.1(5) . . ? C13 O3 C12 110.7(5) . . ? C1 N1 P1 125.1(4) . . ? C1 N1 H1 117.5 . . ? P1 N1 H1 117.5 . . ? C7 N2 C10 110.6(5) . . ? C7 N2 P1 122.1(4) . . ? C10 N2 P1 126.5(4) . . ? C11 N3 C14 110.3(5) . . ? C11 N3 P1 122.0(4) . . ? C14 N3 P1 118.1(4) . . ? C6 C1 C2 120.0(6) . . ? C6 C1 N1 120.6(5) . . ? C2 C1 N1 119.4(5) . . ? C3 C2 C1 119.6(6) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 119.5(6) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? F1 C4 C5 119.0(6) . . ? F1 C4 C3 119.0(6) . . ? C5 C4 C3 122.0(6) . . ? C4 C5 C6 119.1(6) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C5 C6 C1 119.7(6) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? N2 C7 C8 110.1(5) . . ? N2 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? N2 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? O2 C8 C7 110.9(5) . . ? O2 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? O2 C9 C10 111.0(5) . . ? O2 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? O2 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? N2 C10 C9 109.9(5) . . ? N2 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? N2 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? N3 C11 C12 110.7(5) . . ? N3 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? N3 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? O3 C12 C11 110.5(5) . . ? O3 C12 H12A 109.5 . . ? C11 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? O3 C13 C14 112.6(6) . . ? O3 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? O3 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? N3 C14 C13 108.5(5) . . ? N3 C14 H14A 110.0 . . ? C13 C14 H14A 110.0 . . ? N3 C14 H14B 110.0 . . ? C13 C14 H14B 110.0 . . ? H14A C14 H14B 108.4 . . ? Ce1 O1W H1W 130.4 . . ? Ce1 O1W H2W 128.1 . . ? H1W O1W H2W 99.7 . . ? 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 O1 Ce1 123.7(14) . . . . ? N1 P1 O1 Ce1 4.9(15) . . . . ? N3 P1 O1 Ce1 -114.0(14) . . . . ? O1W Ce1 O1 P1 121.3(14) . . . . ? O1W Ce1 O1 P1 -20.9(14) 2 . . . ? Cl2 Ce1 O1 P1 49.7(14) . . . . ? Cl1 Ce1 O1 P1 -171.1(14) 2 . . . ? Cl1 Ce1 O1 P1 -90.2(14) . . . . ? O1 P1 N1 C1 63.3(5) . . . . ? N2 P1 N1 C1 -57.5(5) . . . . ? N3 P1 N1 C1 -176.4(5) . . . . ? O1 P1 N2 C7 15.8(5) . . . . ? N1 P1 N2 C7 140.3(5) . . . . ? N3 P1 N2 C7 -104.6(5) . . . . ? O1 P1 N2 C10 -152.6(5) . . . . ? N1 P1 N2 C10 -28.0(6) . . . . ? N3 P1 N2 C10 87.0(6) . . . . ? O1 P1 N3 C11 -172.8(5) . . . . ? N2 P1 N3 C11 -52.0(6) . . . . ? N1 P1 N3 C11 62.7(5) . . . . ? O1 P1 N3 C14 44.3(5) . . . . ? N2 P1 N3 C14 165.1(4) . . . . ? N1 P1 N3 C14 -80.2(5) . . . . ? P1 N1 C1 C6 -16.8(8) . . . . ? P1 N1 C1 C2 164.6(5) . . . . ? C6 C1 C2 C3 0.9(9) . . . . ? N1 C1 C2 C3 179.5(6) . . . . ? C1 C2 C3 C4 0.8(9) . . . . ? C2 C3 C4 F1 178.7(6) . . . . ? C2 C3 C4 C5 -2.2(10) . . . . ? F1 C4 C5 C6 -179.1(6) . . . . ? C3 C4 C5 C6 1.8(10) . . . . ? C4 C5 C6 C1 0.0(10) . . . . ? C2 C1 C6 C5 -1.3(9) . . . . ? N1 C1 C6 C5 -179.9(6) . . . . ? C10 N2 C7 C8 -57.3(7) . . . . ? P1 N2 C7 C8 132.7(5) . . . . ? C9 O2 C8 C7 -56.3(7) . . . . ? N2 C7 C8 O2 56.3(7) . . . . ? C8 O2 C9 C10 55.8(7) . . . . ? C7 N2 C10 C9 56.6(7) . . . . ? P1 N2 C10 C9 -134.0(5) . . . . ? O2 C9 C10 N2 -55.2(7) . . . . ? C14 N3 C11 C12 -56.3(7) . . . . ? P1 N3 C11 C12 158.2(5) . . . . ? C13 O3 C12 C11 -58.2(7) . . . . ? N3 C11 C12 O3 57.4(7) . . . . ? C12 O3 C13 C14 59.5(7) . . . . ? C11 N3 C14 C13 55.1(7) . . . . ? P1 N3 C14 C13 -157.9(5) . . . . ? O3 C13 C14 N3 -57.3(7) . . . . ? 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 _geom_hbond_publ_flag N1 H1 Cl1 0.88 2.585 3.420(5) 158.8 10_454 ? O1W H1W O2 0.85 1.862 2.712(6) 179.7 9_554 ? O1W H2W O3 0.85 1.982 2.832(6) 179.6 3_555 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 3.017 _refine_diff_density_min -0.999 _refine_diff_density_rms 0.126 _publ_section_references ; Bruker (2005). APEX2 softwarwe package, Bruker AXS Inc., 5465, East Cheryl Parkway, Madison, WI 5317. Sheldrick G.M. (1998). SHELXTL v. 5.10, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; There is a high positive residual density of 3.0 e\%A^-3^ near the Ce1 center (distance 1.0%A) due to considerable absorption effects which could not be completely corrected. Hydrogen atoms were placed in geometrically calculated positions and refined in isotropic approximation in riding model with the Uiso(H) parameters equal to 1.5Ueq(Oi) for water molecules and to 1.2Ueq(Ci) for carbon atoms where Ueq(O) and Ueq(C) are the equivalent thermal parameters of the atoms to which corresponding H atoms are bonded. ; # end Validation Reply Form data_NdHPA #TrackingRef '- Stractures.CIF' _database_code_depnum_ccdc_archive 'CCDC 741995' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H48 Cl3 N6 Nd O8 P2' _chemical_formula_sum 'C28 H48 Cl3 N6 Nd O8 P2' _chemical_formula_weight 909.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'F d d 2' _symmetry_space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 14.3982(5) _cell_length_b 39.9500(13) _cell_length_c 12.9910(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7472.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 668 _cell_measurement_theta_min 3 _cell_measurement_theta_max 29 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3704 _exptl_absorpt_coefficient_mu 1.743 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.537 _exptl_absorpt_correction_T_max 0.695 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type "Bruker APEX II CCD area detector'" _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22356 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -54 _diffrn_reflns_limit_k_max 54 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 29.00 _reflns_number_total 4955 _reflns_number_gt 4590 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0212P)^2^+] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.009(7) _refine_ls_number_reflns 4955 _refine_ls_number_parameters 230 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0244 _refine_ls_R_factor_gt 0.0213 _refine_ls_wR_factor_ref 0.0447 _refine_ls_wR_factor_gt 0.0439 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 Nd1 Nd 0.5000 0.0000 0.002280(11) 0.02710(4) Uani 1 2 d S . . Cl1 Cl 0.57982(5) -0.035243(17) -0.16368(5) 0.04266(15) Uani 1 1 d . . . Cl2 Cl 0.5000 0.0000 0.21310(7) 0.0526(3) Uani 1 2 d S . . P1 P 0.26035(4) -0.038812(15) 0.04122(5) 0.02983(13) Uani 1 1 d . . . N1 N 0.19585(15) -0.01380(5) 0.11121(17) 0.0348(5) Uani 1 1 d . . . H1N H 0.183(2) -0.0200(7) 0.163(2) 0.039(8) Uiso 1 1 d . . . N2 N 0.26960(14) -0.07401(5) 0.10689(17) 0.0353(5) Uani 1 1 d . . . N3 N 0.20379(14) -0.04443(5) -0.06569(16) 0.0331(4) Uani 1 1 d . . . O1 O 0.35504(11) -0.02617(4) 0.01834(14) 0.0383(4) Uani 1 1 d . . . O2 O 0.28758(15) -0.13186(5) 0.22878(17) 0.0566(6) Uani 1 1 d . . . O3 O 0.11601(14) -0.07538(5) -0.23591(15) 0.0473(4) Uani 1 1 d . . . C1 C 0.16936(17) 0.01926(6) 0.0841(2) 0.0336(5) Uani 1 1 d . . . C2 C 0.09865(19) 0.03451(7) 0.1403(2) 0.0415(6) Uani 1 1 d . . . H2A H 0.0678 0.0229 0.1921 0.050 Uiso 1 1 calc R . . C3 C 0.0751(2) 0.06765(9) 0.1171(3) 0.0524(8) Uani 1 1 d . . . H3A H 0.0283 0.0782 0.1543 0.063 Uiso 1 1 calc R . . C4 C 0.1202(2) 0.08486(8) 0.0401(2) 0.0558(8) Uani 1 1 d . . . H4A H 0.1039 0.1069 0.0253 0.067 Uiso 1 1 calc R . . C5 C 0.1893(2) 0.06935(7) -0.0147(2) 0.0488(7) Uani 1 1 d . . . H5A H 0.2197 0.0809 -0.0671 0.059 Uiso 1 1 calc R . . C6 C 0.21418(19) 0.03665(6) 0.0075(3) 0.0401(5) Uani 1 1 d . . . H6A H 0.2615 0.0264 -0.0296 0.048 Uiso 1 1 calc R . . C7 C 0.3361(2) -0.07561(7) 0.1922(2) 0.0501(7) Uani 1 1 d . . . H7A H 0.3076 -0.0671 0.2545 0.060 Uiso 1 1 calc R . . H7B H 0.3899 -0.0619 0.1766 0.060 Uiso 1 1 calc R . . C8 C 0.3653(2) -0.11105(8) 0.2079(3) 0.0580(8) Uani 1 1 d . . . H8A H 0.3969 -0.1190 0.1467 0.070 Uiso 1 1 calc R . . H8B H 0.4087 -0.1122 0.2650 0.070 Uiso 1 1 calc R . . C9 C 0.2233(3) -0.13067(8) 0.1460(3) 0.0597(9) Uani 1 1 d . . . H9A H 0.1706 -0.1449 0.1618 0.072 Uiso 1 1 calc R . . H9B H 0.2528 -0.1393 0.0843 0.072 Uiso 1 1 calc R . . C10 C 0.18987(19) -0.09578(7) 0.1264(2) 0.0449(6) Uani 1 1 d . . . H10A H 0.1487 -0.0956 0.0673 0.054 Uiso 1 1 calc R . . H10B H 0.1556 -0.0877 0.1856 0.054 Uiso 1 1 calc R . . C11 C 0.2506(2) -0.04715(7) -0.16530(19) 0.0431(6) Uani 1 1 d . . . H11A H 0.3169 -0.0495 -0.1549 0.052 Uiso 1 1 calc R . . H11B H 0.2398 -0.0270 -0.2052 0.052 Uiso 1 1 calc R . . C12 C 0.2138(2) -0.07705(7) -0.2227(2) 0.0484(7) Uani 1 1 d . . . H12A H 0.2434 -0.0783 -0.2897 0.058 Uiso 1 1 calc R . . H12B H 0.2294 -0.0973 -0.1851 0.058 Uiso 1 1 calc R . . C13 C 0.0689(2) -0.07139(9) -0.1409(2) 0.0491(8) Uani 1 1 d . . . H13A H 0.0763 -0.0916 -0.1005 0.059 Uiso 1 1 calc R . . H13B H 0.0031 -0.0685 -0.1543 0.059 Uiso 1 1 calc R . . C14 C 0.10299(17) -0.04211(7) -0.0790(2) 0.0398(6) Uani 1 1 d . . . H14A H 0.0875 -0.0214 -0.1141 0.048 Uiso 1 1 calc R . . H14B H 0.0729 -0.0420 -0.0122 0.048 Uiso 1 1 calc R . . O1W O 0.55674(17) -0.05454(5) 0.06565(18) 0.0454(5) Uani 1 1 d . . . H1W H 0.571(3) -0.0581(9) 0.120(3) 0.063(12) Uiso 1 1 d . . . H2W H 0.557(3) -0.0712(10) 0.042(3) 0.070(13) Uiso 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 Nd1 0.02810(7) 0.02670(7) 0.02649(7) 0.000 0.000 -0.00238(9) Cl1 0.0503(4) 0.0454(3) 0.0323(3) -0.0037(3) 0.0012(3) 0.0073(3) Cl2 0.0889(8) 0.0406(5) 0.0284(4) 0.000 0.000 0.0151(5) P1 0.0303(3) 0.0290(3) 0.0302(3) 0.0040(2) -0.0004(3) -0.0029(2) N1 0.0429(12) 0.0350(11) 0.0264(11) 0.0032(9) 0.0024(9) -0.0012(9) N2 0.0333(11) 0.0327(10) 0.0399(11) 0.0099(9) -0.0048(9) -0.0049(8) N3 0.0308(11) 0.0418(12) 0.0267(10) -0.0006(9) 0.0011(8) -0.0029(9) O1 0.0325(8) 0.0391(9) 0.0432(10) 0.0089(8) -0.0010(8) -0.0059(7) O2 0.0720(14) 0.0370(10) 0.0608(15) 0.0173(9) -0.0184(11) -0.0066(9) O3 0.0535(11) 0.0527(11) 0.0356(10) -0.0049(9) -0.0095(9) -0.0052(9) C1 0.0346(13) 0.0314(12) 0.0346(12) -0.0035(10) -0.0048(10) -0.0015(9) C2 0.0376(14) 0.0502(16) 0.0366(14) -0.0060(12) -0.0023(11) 0.0007(12) C3 0.0446(17) 0.0549(19) 0.058(2) -0.0153(16) -0.0084(16) 0.0134(14) C4 0.070(2) 0.0387(15) 0.0589(19) -0.0044(13) -0.0153(16) 0.0147(14) C5 0.0619(18) 0.0379(14) 0.0467(18) 0.0062(12) -0.0061(14) -0.0006(12) C6 0.0445(14) 0.0368(13) 0.0391(14) 0.0026(13) 0.0049(14) 0.0046(11) C7 0.0564(18) 0.0431(16) 0.0507(17) 0.0164(13) -0.0199(14) -0.0133(13) C8 0.0489(17) 0.0575(19) 0.068(2) 0.0206(16) -0.0171(15) 0.0007(14) C9 0.081(2) 0.0352(15) 0.063(2) 0.0101(14) -0.0257(17) -0.0154(15) C10 0.0397(15) 0.0416(14) 0.0534(16) 0.0143(13) -0.0034(13) -0.0102(11) C11 0.0481(15) 0.0484(15) 0.0327(13) -0.0027(11) 0.0061(13) -0.0095(12) C12 0.0537(16) 0.0496(16) 0.0420(16) -0.0084(12) 0.0047(12) -0.0040(13) C13 0.0438(16) 0.063(2) 0.0402(16) 0.0031(15) -0.0064(13) -0.0116(15) C14 0.0321(13) 0.0501(16) 0.0372(14) -0.0011(12) -0.0042(11) 0.0030(11) O1W 0.0693(15) 0.0321(11) 0.0349(11) -0.0022(9) -0.0082(10) 0.0113(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 Nd1 O1 2.3437(15) 2_655 ? Nd1 O1 2.3437(15) . ? Nd1 O1W 2.468(2) . ? Nd1 O1W 2.468(2) 2_655 ? Nd1 Cl2 2.7387(9) . ? Nd1 Cl1 2.8199(6) 2_655 ? Nd1 Cl1 2.8199(6) . ? P1 O1 1.4839(17) . ? P1 N3 1.626(2) . ? P1 N1 1.640(2) . ? P1 N2 1.650(2) . ? N1 C1 1.419(3) . ? N1 H1N 0.74(3) . ? N2 C10 1.462(3) . ? N2 C7 1.466(3) . ? N3 C11 1.463(3) . ? N3 C14 1.465(3) . ? O2 C9 1.419(4) . ? O2 C8 1.421(4) . ? O3 C13 1.418(4) . ? O3 C12 1.419(4) . ? C1 C6 1.374(4) . ? C1 C2 1.393(4) . ? C2 C3 1.399(4) . ? C2 H2A 0.9300 . ? C3 C4 1.377(5) . ? C3 H3A 0.9300 . ? C4 C5 1.371(4) . ? C4 H4A 0.9300 . ? C5 C6 1.385(4) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.491(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.497(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.505(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.502(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? O1W H1W 0.75(4) . ? O1W H2W 0.73(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 O1 Nd1 O1 169.78(9) 2_655 . ? O1 Nd1 O1W 93.98(7) 2_655 . ? O1 Nd1 O1W 82.60(7) . . ? O1 Nd1 O1W 82.60(7) 2_655 2_655 ? O1 Nd1 O1W 93.98(7) . 2_655 ? O1W Nd1 O1W 141.03(11) . 2_655 ? O1 Nd1 Cl2 84.89(4) 2_655 . ? O1 Nd1 Cl2 84.89(4) . . ? O1W Nd1 Cl2 70.52(5) . . ? O1W Nd1 Cl2 70.52(5) 2_655 . ? O1 Nd1 Cl1 102.02(5) 2_655 2_655 ? O1 Nd1 Cl1 85.86(4) . 2_655 ? O1W Nd1 Cl1 146.16(6) . 2_655 ? O1W Nd1 Cl1 71.30(6) 2_655 2_655 ? Cl2 Nd1 Cl1 139.870(14) . 2_655 ? O1 Nd1 Cl1 85.86(4) 2_655 . ? O1 Nd1 Cl1 102.02(5) . . ? O1W Nd1 Cl1 71.30(6) . . ? O1W Nd1 Cl1 146.16(6) 2_655 . ? Cl2 Nd1 Cl1 139.869(14) . . ? Cl1 Nd1 Cl1 80.26(3) 2_655 . ? O1 P1 N3 109.64(11) . . ? O1 P1 N1 115.10(11) . . ? N3 P1 N1 105.91(11) . . ? O1 P1 N2 108.63(10) . . ? N3 P1 N2 111.38(11) . . ? N1 P1 N2 106.16(11) . . ? C1 N1 P1 125.57(18) . . ? C1 N1 H1N 118(2) . . ? P1 N1 H1N 116(2) . . ? C10 N2 C7 110.9(2) . . ? C10 N2 P1 122.20(17) . . ? C7 N2 P1 118.73(17) . . ? C11 N3 C14 110.9(2) . . ? C11 N3 P1 122.37(17) . . ? C14 N3 P1 126.07(17) . . ? P1 O1 Nd1 171.05(12) . . ? C9 O2 C8 110.5(2) . . ? C13 O3 C12 112.0(2) . . ? C6 C1 C2 120.1(2) . . ? C6 C1 N1 121.6(2) . . ? C2 C1 N1 118.2(2) . . ? C1 C2 C3 118.5(3) . . ? C1 C2 H2A 120.7 . . ? C3 C2 H2A 120.7 . . ? C4 C3 C2 121.0(3) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C6 120.3(3) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C1 C6 C5 120.4(3) . . ? C1 C6 H6A 119.8 . . ? C5 C6 H6A 119.8 . . ? N2 C7 C8 109.2(2) . . ? N2 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N2 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? O2 C8 C7 111.0(3) . . ? O2 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? O2 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? O2 C9 C10 111.7(2) . . ? O2 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? O2 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? N2 C10 C9 109.3(2) . . ? N2 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? N2 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? N3 C11 C12 109.6(2) . . ? N3 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? N3 C11 H11B 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.2 . . ? O3 C12 C11 111.8(2) . . ? O3 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? O3 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? O3 C13 C14 113.4(3) . . ? O3 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? O3 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? N3 C14 C13 109.8(2) . . ? N3 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? N3 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? Nd1 O1W H1W 125(3) . . ? Nd1 O1W H2W 132(3) . . ? H1W O1W H2W 103(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 O1 P1 N1 C1 60.2(2) . . . . ? N3 P1 N1 C1 -61.1(2) . . . . ? N2 P1 N1 C1 -179.62(19) . . . . ? O1 P1 N2 C10 -169.4(2) . . . . ? N3 P1 N2 C10 -48.5(2) . . . . ? N1 P1 N2 C10 66.3(2) . . . . ? O1 P1 N2 C7 45.0(2) . . . . ? N3 P1 N2 C7 165.9(2) . . . . ? N1 P1 N2 C7 -79.3(2) . . . . ? O1 P1 N3 C11 18.4(2) . . . . ? N1 P1 N3 C11 143.1(2) . . . . ? N2 P1 N3 C11 -101.9(2) . . . . ? O1 P1 N3 C14 -151.2(2) . . . . ? N1 P1 N3 C14 -26.5(2) . . . . ? N2 P1 N3 C14 88.5(2) . . . . ? P1 N1 C1 C6 -16.5(3) . . . . ? P1 N1 C1 C2 166.2(2) . . . . ? C6 C1 C2 C3 -0.2(4) . . . . ? N1 C1 C2 C3 177.1(2) . . . . ? C1 C2 C3 C4 0.4(5) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C3 C4 C5 C6 -0.4(5) . . . . ? C2 C1 C6 C5 -0.2(4) . . . . ? N1 C1 C6 C5 -177.4(2) . . . . ? C4 C5 C6 C1 0.6(4) . . . . ? C10 N2 C7 C8 56.7(3) . . . . ? P1 N2 C7 C8 -154.0(2) . . . . ? C9 O2 C8 C7 59.4(4) . . . . ? N2 C7 C8 O2 -58.3(3) . . . . ? C8 O2 C9 C10 -58.6(4) . . . . ? C7 N2 C10 C9 -55.7(3) . . . . ? P1 N2 C10 C9 156.4(2) . . . . ? O2 C9 C10 N2 56.6(4) . . . . ? C14 N3 C11 C12 -57.2(3) . . . . ? P1 N3 C11 C12 131.8(2) . . . . ? C13 O3 C12 C11 -55.2(3) . . . . ? N3 C11 C12 O3 56.9(3) . . . . ? C12 O3 C13 C14 53.9(3) . . . . ? C11 N3 C14 C13 55.3(3) . . . . ? P1 N3 C14 C13 -134.1(2) . . . . ? O3 C13 C14 N3 -53.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1N Cl1 9_455 0.74(3) 2.77(3) 3.475(2) 161(1) ? O1W H1W O3 9_555 0.75(4) 2.10(4) 2.840(4) 172(3) ? O1W H2W O2 7_544 0.73(4) 2.07(4) 2.794(4) 172(3) ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.550 _refine_diff_density_min -0.518 _refine_diff_density_rms 0.056 _publ_section_references ; Bruker, Programs APEX II, version 2.0-1; SAINT, version 7.23A; SADABS, version 2004/1; XPREP, version 2005/2; SHELXTL, version 6.1. Bruker AXS Inc., Madison, WI, USA, 2005. G.M. Sheldrick, Programs SHELXS97 (crystal structure solution) and SHELXL97 (crystal structure refinement), University of Gottingen, Germany, 1997. ; _publ_section_exptl_refinement ; The hydrogen atoms of water molecule and NH group were found in the difference Fourier synthesis and refined in isotropic approximation. The H(C) atom positions were calculated and refined in isotropic approximatiom within riding model with the Uiso(H) parameters equal to 1.2 Ueq(Ci), where U(Ci) are the equivalent thermal parameters of the atoms to which corresponding H atoms are bonded. ; # start Validation Reply Form _vrf_PLAT232_57 ; PROBLEM: Hirshfeld Test Diff (M-X) Nd1 -- Cl1 .. 14.11 su RESPONSE: The significant differences for the M-X bond involving the lanthanide atom are apparently caused by the absorption effects that were not fully accounted for. # end Validation Reply Form ;