#============================================================================== data_global #============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name 'Prof. Dr. M. N. Bochkarev' _publ_contact_author_address ; Razuvaev Institute of Organometallic Chemistry Russian Academy of Sciences Tropinina 49 603950 Nizhny Novgorod Russia ; _publ_contact_author_email 'mboch@imoc.sinn.ru' _publ_contact_author_fax '(8312)66-67-95' _publ_contact_author_phone '(8312)66-14-97' _publ_requested_journal 'J. Am. Chem. Soc.' _publ_requested_coeditor_name ? #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; A Novel di(imine)amine Ligands as a Result of Acetonitrile Coupling with Diiodides of Nd(II), Dy(II), and Tm(II) ; loop_ _publ_author_name _publ_author_address 'Bochkarev, Mikhail N.' ; Razuvaev Institute of Organometallic Chemistry Russian Academy of Sciences Tropinina 49 603950 Nizhny Novgorod Russia ; 'Khoroshenkov, Georgii V.' ; Razuvaev Institute of Organometallic Chemistry Russian Academy of Sciences Tropinina 49 603950 Nizhny Novgorod Russia ; 'Schumann, Herbert' ; Institut f\"ur Chemie Technische Universit\"at Berlin Stra\&se des 17. Juni 135 D-10623 Berlin Germany ; 'Dechert, Sebastian' ; Institut f\"ur Chemie Technische Universit\"at Berlin Stra\&se des 17. Juni 135 D-10623 Berlin Germany ; #============================================================================== data_Ib _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H31 Dy N9 3+, 3 I 1-, 4(C2 H3 N)' _chemical_formula_sum 'C26 H43 Dy I3 N13' _chemical_formula_weight 1080.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Dy' 'Dy' -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 20.3218(3) _cell_length_b 13.8313(1) _cell_length_c 15.4992(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4356.47(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7779 _cell_measurement_theta_min 1.97 _cell_measurement_theta_max 30.62 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2060 _exptl_absorpt_coefficient_mu 3.872 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.329393 _exptl_absorpt_correction_T_max 0.545187 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 30673 _diffrn_reflns_av_R_equivalents 0.0740 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4911 _reflns_number_gt 4000 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ZORTEP (Zsolnai, Pritzkow, 1994)' _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^)+(0.0482P)^2^+9.8274P] 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 4911 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.0995 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Dy Dy 0.425321(16) 0.2500 0.65016(2) 0.02068(10) Uani 1 2 d S . . I1 I 0.653527(19) 0.48235(3) 0.61469(3) 0.03640(12) Uani 1 1 d . . . I2 I 0.91018(3) 0.7500 0.70406(4) 0.03603(14) Uani 1 2 d S . . N1 N 0.5444(3) 0.2500 0.6066(4) 0.0240(13) Uani 1 2 d S . . H1A H 0.5647 0.3028 0.6276 0.080 Uiso 0.50 1 calc PR . . H1B H 0.5647 0.1972 0.6276 0.080 Uiso 0.50 1 calc PR . . N2 N 0.4561(2) 0.3564(3) 0.5303(3) 0.0221(9) Uani 1 1 d . . . H2 H 0.4324 0.4065 0.5194 0.080 Uiso 1 1 calc R . . C1 C 0.5470(3) 0.2500 0.5108(4) 0.0193(14) Uani 1 2 d S . . C2 C 0.6168(4) 0.2500 0.4747(5) 0.0254(15) Uani 1 2 d S . . H2A H 0.6398 0.3064 0.4947 0.080 Uiso 0.50 1 calc PR . . H2B H 0.6152 0.2505 0.4128 0.080 Uiso 1 2 calc SR . . H2C H 0.6396 0.1931 0.4940 0.080 Uiso 0.50 1 calc PR . . C3 C 0.5067(2) 0.3390(3) 0.4838(3) 0.0194(10) Uani 1 1 d . . . C4 C 0.5262(3) 0.3952(4) 0.4061(4) 0.0291(12) Uani 1 1 d . . . H4A H 0.4927 0.4420 0.3932 0.080 Uiso 1 1 calc R . . H4B H 0.5314 0.3522 0.3580 0.080 Uiso 1 1 calc R . . H4C H 0.5670 0.4279 0.4170 0.080 Uiso 1 1 calc R . . N3 N 0.3567(2) 0.4018(3) 0.6644(3) 0.0305(10) Uani 1 1 d . . . C5 C 0.3240(3) 0.4685(4) 0.6665(4) 0.0317(12) Uani 1 1 d . . . C6 C 0.2826(3) 0.5529(5) 0.6687(5) 0.0503(18) Uani 1 1 d . . . H6A H 0.2697 0.5697 0.6111 0.080 Uiso 1 1 calc R . . H6B H 0.3065 0.6058 0.6940 0.080 Uiso 1 1 calc R . . H6C H 0.2442 0.5396 0.7026 0.080 Uiso 1 1 calc R . . N4 N 0.4849(2) 0.3674(3) 0.7442(3) 0.0321(10) Uani 1 1 d . . . C7 C 0.5080(3) 0.4315(4) 0.7784(4) 0.0294(12) Uani 1 1 d . . . C8 C 0.5376(4) 0.5135(5) 0.8217(5) 0.0494(17) Uani 1 1 d . . . H8A H 0.5302 0.5709 0.7883 0.080 Uiso 1 1 calc R . . H8B H 0.5840 0.5029 0.8277 0.080 Uiso 1 1 calc R . . H8C H 0.5181 0.5210 0.8778 0.080 Uiso 1 1 calc R . . N5 N 0.3644(3) 0.2500 0.7928(4) 0.0329(15) Uani 1 2 d S . . C9 C 0.3337(4) 0.2500 0.8535(6) 0.0368(19) Uani 1 2 d S . . C10 C 0.2930(6) 0.2500 0.9304(7) 0.057(3) Uani 1 2 d S . . H10A H 0.2671 0.3080 0.9319 0.080 Uiso 0.50 1 calc PR . . H10B H 0.3206 0.2472 0.9806 0.080 Uiso 1 2 calc SR . . H10C H 0.2644 0.1948 0.9294 0.080 Uiso 0.50 1 calc PR . . N6 N 0.3328(3) 0.2500 0.5455(5) 0.0320(15) Uani 1 2 d S . . C11 C 0.2976(4) 0.2500 0.4890(5) 0.0330(18) Uani 1 2 d S . . C12 C 0.2516(5) 0.2500 0.4159(7) 0.054(3) Uani 1 2 d S . . H12A H 0.2583 0.3071 0.3819 0.080 Uiso 0.50 1 calc PR . . H12B H 0.2072 0.2491 0.4372 0.080 Uiso 1 2 calc SR . . H12C H 0.2591 0.1938 0.3810 0.080 Uiso 0.50 1 calc PR . . N7 N 0.1926(7) 0.7500 0.6542(8) 0.090(4) Uani 1 2 d S . . C13 C 0.1526(6) 0.7500 0.7046(9) 0.060(3) Uani 1 2 d S . . C14 C 0.1050(5) 0.7500 0.7735(9) 0.062(3) Uani 1 2 d S . . H14A H 0.1137 0.6969 0.8118 0.080 Uiso 0.50 1 calc PR . . H14B H 0.0616 0.7433 0.7498 0.080 Uiso 0.50 1 calc PR . . H14C H 0.1079 0.8097 0.8049 0.080 Uiso 0.50 1 calc PR . . N8 N 0.5384(8) 0.262(3) 0.9614(9) 0.103(6) Uiso 0.50 1 d P A -1 C15 C 0.4841(8) 0.3103(11) 0.9851(10) 0.059(4) Uiso 0.50 1 d P A -1 C16 C 0.4379(3) 0.3905(5) 0.9893(4) 0.117(8) Uiso 0.50 1 d P A -1 H16A H 0.4616 0.4505 0.9881 0.080 Uiso 0.50 1 calc PR A -1 H16B H 0.4129 0.3864 1.0418 0.080 Uiso 0.50 1 calc PR A -1 H16C H 0.4086 0.3876 0.9408 0.080 Uiso 0.50 1 calc PR A -1 N9 N 0.3315(3) 0.5884(6) 1.0665(4) 0.078(4) Uiso 0.50 1 d PR A -2 C17 C 0.3382(3) 0.5532(5) 0.9886(5) 0.064(4) Uiso 0.50 1 d PR A -2 C18 C 0.3457(4) 0.5132(5) 0.9089(4) 0.027(2) Uiso 0.50 1 d PR A -2 H18A H 0.3750 0.4589 0.9126 0.080 Uiso 0.50 1 calc PR A -2 H18B H 0.3636 0.5604 0.8701 0.080 Uiso 0.50 1 calc PR A -2 H18C H 0.3037 0.4919 0.8879 0.080 Uiso 0.50 1 calc PR A -2 N10 N 0.3241(3) 0.8678(5) 1.1084(5) 0.088(5) Uiso 0.50 1 d PR A -2 C19 C 0.3206(3) 0.8162(5) 1.1571(5) 0.057(4) Uiso 0.50 1 d PR A -2 C20 C 0.3117(3) 0.7445(6) 1.2188(4) 0.071(3) Uiso 0.50 1 d PR A -2 H20A H 0.2675 0.7204 1.2154 0.080 Uiso 0.50 1 calc PR A -2 H20B H 0.3193 0.7709 1.2752 0.080 Uiso 0.50 1 calc PR A -2 H20C H 0.3421 0.6926 1.2084 0.080 Uiso 0.50 1 calc PR A -2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Dy 0.02027(17) 0.02210(17) 0.01966(17) 0.000 0.00157(13) 0.000 I1 0.0318(2) 0.02887(19) 0.0485(3) -0.00214(16) -0.00512(17) 0.00000(15) I2 0.0361(3) 0.0411(3) 0.0308(3) 0.000 -0.0097(2) 0.000 N1 0.026(3) 0.026(3) 0.020(3) 0.000 0.000(2) 0.000 N2 0.023(2) 0.021(2) 0.022(2) 0.0008(17) 0.0000(17) 0.0045(17) C1 0.016(3) 0.021(3) 0.021(4) 0.000 0.003(3) 0.000 C2 0.020(4) 0.029(4) 0.027(4) 0.000 0.001(3) 0.000 C3 0.025(2) 0.015(2) 0.018(2) 0.0016(18) -0.0016(19) -0.0031(19) C4 0.035(3) 0.020(2) 0.032(3) 0.005(2) 0.006(2) 0.001(2) N3 0.031(2) 0.032(2) 0.029(3) 0.001(2) 0.0020(19) 0.003(2) C5 0.032(3) 0.030(3) 0.033(3) 0.000(2) 0.007(2) -0.002(2) C6 0.032(3) 0.035(3) 0.084(5) -0.011(3) 0.005(3) 0.008(3) N4 0.033(3) 0.035(3) 0.029(3) -0.003(2) 0.002(2) -0.001(2) C7 0.031(3) 0.028(3) 0.029(3) -0.001(2) -0.003(2) 0.002(2) C8 0.055(4) 0.035(3) 0.058(4) -0.013(3) -0.020(4) 0.001(3) N5 0.034(4) 0.034(4) 0.030(4) 0.000 0.010(3) 0.000 C9 0.035(5) 0.032(4) 0.043(5) 0.000 0.004(4) 0.000 C10 0.059(7) 0.071(7) 0.042(6) 0.000 0.020(5) 0.000 N6 0.025(3) 0.031(3) 0.040(4) 0.000 -0.004(3) 0.000 C11 0.034(4) 0.034(4) 0.032(5) 0.000 -0.003(4) 0.000 C12 0.046(6) 0.056(6) 0.059(7) 0.000 -0.023(5) 0.000 N7 0.106(11) 0.083(8) 0.079(8) 0.000 -0.005(8) 0.000 C13 0.062(8) 0.038(6) 0.081(9) 0.000 -0.010(7) 0.000 C14 0.039(6) 0.035(5) 0.112(10) 0.000 -0.014(6) 0.000 _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 Dy N2 2.451(4) 7_565 ? Dy N2 2.451(4) . ? Dy N6 2.483(7) . ? Dy N4 2.496(5) . ? Dy N4 2.496(5) 7_565 ? Dy N1 2.512(6) . ? Dy N3 2.530(5) . ? Dy N3 2.530(5) 7_565 ? Dy N5 2.534(7) . ? N1 C1 1.485(9) . ? N2 C3 1.279(6) . ? C1 C2 1.526(9) . ? C1 C3 1.536(6) 7_565 ? C1 C3 1.536(6) . ? C3 C4 1.487(7) . ? N3 C5 1.138(7) . ? C5 C6 1.439(8) . ? N4 C7 1.135(7) . ? C7 C8 1.448(8) . ? N5 C9 1.128(10) . ? C9 C10 1.451(13) . ? N6 C11 1.131(10) . ? C11 C12 1.469(12) . ? N7 C13 1.126(17) . ? C13 C14 1.442(18) . ? N8 C15 1.34(3) . ? C15 C16 1.455(17) . ? N9 C17 1.3082(18) . ? C17 C18 1.3619(17) . ? N10 C19 1.042(2) . ? C19 C20 1.3891(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Dy N2 73.82(19) 7_565 . ? N2 Dy N6 72.46(16) 7_565 . ? N2 Dy N6 72.46(16) . . ? N2 Dy N4 135.18(15) 7_565 . ? N2 Dy N4 85.88(15) . . ? N6 Dy N4 138.52(11) . . ? N2 Dy N4 85.88(15) 7_565 7_565 ? N2 Dy N4 135.17(15) . 7_565 ? N6 Dy N4 138.52(11) . 7_565 ? N4 Dy N4 81.1(2) . 7_565 ? N2 Dy N1 63.27(14) 7_565 . ? N2 Dy N1 63.27(14) . . ? N6 Dy N1 123.6(2) . . ? N4 Dy N1 71.92(15) . . ? N4 Dy N1 71.92(15) 7_565 . ? N2 Dy N3 134.84(14) 7_565 . ? N2 Dy N3 73.05(14) . . ? N6 Dy N3 68.88(13) . . ? N4 Dy N3 71.15(15) . . ? N4 Dy N3 139.14(15) 7_565 . ? N1 Dy N3 123.66(11) . . ? N2 Dy N3 73.05(14) 7_565 7_565 ? N2 Dy N3 134.84(14) . 7_565 ? N6 Dy N3 68.88(13) . 7_565 ? N4 Dy N3 139.14(15) . 7_565 ? N4 Dy N3 71.15(15) 7_565 7_565 ? N1 Dy N3 123.66(11) . 7_565 ? N3 Dy N3 112.2(2) . 7_565 ? N2 Dy N5 141.80(10) 7_565 . ? N2 Dy N5 141.80(10) . . ? N6 Dy N5 101.5(2) . . ? N4 Dy N5 74.19(16) . . ? N4 Dy N5 74.19(16) 7_565 . ? N1 Dy N5 134.9(2) . . ? N3 Dy N5 69.80(13) . . ? N3 Dy N5 69.80(13) 7_565 . ? C1 N1 Dy 107.6(4) . . ? C3 N2 Dy 121.3(3) . . ? N1 C1 C2 113.6(6) . . ? N1 C1 C3 104.7(4) . 7_565 ? C2 C1 C3 113.3(4) . 7_565 ? N1 C1 C3 104.7(4) . . ? C2 C1 C3 113.3(4) . . ? C3 C1 C3 106.5(5) 7_565 . ? N2 C3 C4 124.9(4) . . ? N2 C3 C1 115.2(4) . . ? C4 C3 C1 119.9(5) . . ? C5 N3 Dy 176.0(5) . . ? N3 C5 C6 179.8(7) . . ? C7 N4 Dy 169.1(4) . . ? N4 C7 C8 179.8(8) . . ? C9 N5 Dy 175.7(7) . . ? N5 C9 C10 178.7(10) . . ? C11 N6 Dy 170.0(7) . . ? N6 C11 C12 179.7(10) . . ? N7 C13 C14 176.0(15) . . ? N8 C15 C16 158(2) . . ? N9 C17 C18 177.8(3) . . ? N10 C19 C20 175.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.831 _refine_diff_density_min -0.952 _refine_diff_density_rms 0.184 #===END data_Ic _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H31 N9 Tm 3+, 3 I 1-, 2(C2 H3 N)' _chemical_formula_sum 'C22 H37 I3 N11 Tm' _chemical_formula_weight 1005.26 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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Tm' 'Tm' -0.3139 5.2483 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7188(3) _cell_length_b 13.7619(5) _cell_length_c 14.0021(5) _cell_angle_alpha 69.641(1) _cell_angle_beta 89.732(1) _cell_angle_gamma 73.989(1) _cell_volume 1851.75(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3647 _cell_measurement_theta_min 1.56 _cell_measurement_theta_max 30.55 _exptl_crystal_description 'irregular shape' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.803 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 948 _exptl_absorpt_coefficient_mu 4.923 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.437734 _exptl_absorpt_correction_T_max 0.694916 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 12405 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0988 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7169 _reflns_number_gt 5054 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ZORTEP (Zsolnai, Pritzkow, 1994)' _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^)+(0.0283P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7169 _refine_ls_number_parameters 344 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1061 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 Tm Tm 0.84081(3) 0.36908(3) 0.29679(3) 0.01939(11) Uani 1 1 d . . . I1 I 0.71338(6) 0.70638(5) -0.08900(5) 0.03748(18) Uani 1 1 d . . . I2 I 1.17123(6) 0.82273(5) 0.14911(5) 0.03582(17) Uani 1 1 d . . . I3 I 0.70549(6) 0.73226(6) 0.43436(5) 0.04392(19) Uani 1 1 d . . . N1 N 1.0793(6) 0.3489(5) 0.3079(5) 0.0220(16) Uani 1 1 d . . . H1A H 1.1149 0.3137 0.3732 0.080 Uiso 1 1 calc R . . H1B H 1.1195 0.3109 0.2699 0.080 Uiso 1 1 calc R . . N2 N 0.9096(6) 0.4910(5) 0.3614(5) 0.0227(16) Uani 1 1 d . . . H2 H 0.8637 0.5164 0.4026 0.080 Uiso 1 1 calc R . . N3 N 0.9143(6) 0.4896(5) 0.1505(5) 0.0220(16) Uani 1 1 d . . . H3 H 0.8710 0.5149 0.0912 0.080 Uiso 1 1 calc R . . N4 N 0.7129(7) 0.3845(6) 0.4449(6) 0.0282(17) Uani 1 1 d . . . N5 N 0.9464(7) 0.2161(6) 0.4518(6) 0.0312(18) Uani 1 1 d . . . N6 N 0.6948(7) 0.2524(6) 0.3346(6) 0.0319(18) Uani 1 1 d . . . N7 N 0.6651(7) 0.5437(6) 0.2372(6) 0.0293(18) Uani 1 1 d . . . N8 N 0.7135(7) 0.3897(6) 0.1375(6) 0.0254(17) Uani 1 1 d . . . N9 N 0.9443(7) 0.2300(6) 0.2297(6) 0.0288(17) Uani 1 1 d . . . C1 C 1.0939(7) 0.4605(6) 0.2684(6) 0.0201(18) Uani 1 1 d . . . C2 C 1.2356(8) 0.4622(8) 0.2694(7) 0.034(2) Uani 1 1 d . . . H2A H 1.2780 0.4242 0.3378 0.080 Uiso 1 1 calc R . . H2B H 1.2383 0.5358 0.2464 0.080 Uiso 1 1 calc R . . H2C H 1.2796 0.4275 0.2248 0.080 Uiso 1 1 calc R . . C3 C 1.0123(8) 0.5174(7) 0.3350(6) 0.0246(19) Uani 1 1 d . . . C4 C 1.0566(9) 0.5986(8) 0.3632(7) 0.036(2) Uani 1 1 d . . . H4A H 0.9890 0.6355 0.3944 0.080 Uiso 1 1 calc R . . H4B H 1.0754 0.6503 0.3027 0.080 Uiso 1 1 calc R . . H4C H 1.1338 0.5623 0.4106 0.080 Uiso 1 1 calc R . . C5 C 1.0165(8) 0.5147(6) 0.1620(6) 0.0218(19) Uani 1 1 d . . . C6 C 1.0627(9) 0.5965(7) 0.0777(7) 0.031(2) Uani 1 1 d . . . H6A H 1.0071 0.6201 0.0155 0.080 Uiso 1 1 calc R . . H6B H 1.1506 0.5637 0.0674 0.080 Uiso 1 1 calc R . . H6C H 1.0599 0.6576 0.0968 0.080 Uiso 1 1 calc R . . C7 C 0.6623(8) 0.3815(7) 0.5141(7) 0.027(2) Uani 1 1 d . . . C8 C 0.5932(9) 0.3776(9) 0.6072(7) 0.040(3) Uani 1 1 d . . . H8A H 0.5654 0.4488 0.6106 0.080 Uiso 1 1 calc R . . H8B H 0.6511 0.3287 0.6670 0.080 Uiso 1 1 calc R . . H8C H 0.5185 0.3528 0.6040 0.080 Uiso 1 1 calc R . . C9 C 0.9998(9) 0.1461(8) 0.5253(7) 0.038(2) Uani 1 1 d . . . C10 C 1.0667(12) 0.0601(9) 0.6162(8) 0.065(4) Uani 1 1 d . . . H10A H 1.1305 0.0821 0.6449 0.080 Uiso 1 1 calc R . . H10B H 1.1094 -0.0026 0.6001 0.080 Uiso 1 1 calc R . . H10C H 1.0053 0.0430 0.6648 0.080 Uiso 1 1 calc R . . C11 C 0.6225(9) 0.2040(8) 0.3490(7) 0.030(2) Uani 1 1 d . . . C12 C 0.5250(10) 0.1426(8) 0.3675(8) 0.046(3) Uani 1 1 d . . . H12A H 0.4780 0.1522 0.4237 0.080 Uiso 1 1 calc R . . H12B H 0.5689 0.0670 0.3837 0.080 Uiso 1 1 calc R . . H12C H 0.4651 0.1689 0.3072 0.080 Uiso 1 1 calc R . . C13 C 0.6169(8) 0.6346(8) 0.2045(7) 0.030(2) Uani 1 1 d . . . C14 C 0.5563(9) 0.7526(7) 0.1579(8) 0.040(2) Uani 1 1 d . . . H14A H 0.5774 0.7783 0.0886 0.080 Uiso 1 1 calc R . . H14B H 0.5885 0.7879 0.1963 0.080 Uiso 1 1 calc R . . H14C H 0.4633 0.7685 0.1583 0.080 Uiso 1 1 calc R . . C15 C 0.6638(8) 0.3853(7) 0.0701(7) 0.029(2) Uani 1 1 d . . . C16 C 0.6020(9) 0.3779(10) -0.0184(8) 0.046(3) Uani 1 1 d . . . H16A H 0.6564 0.3185 -0.0343 0.080 Uiso 1 1 calc R . . H16B H 0.5903 0.4441 -0.0759 0.080 Uiso 1 1 calc R . . H16C H 0.5187 0.3663 -0.0033 0.080 Uiso 1 1 calc R . . C17 C 0.9881(8) 0.1816(7) 0.1795(7) 0.029(2) Uani 1 1 d . . . C18 C 1.0400(10) 0.1225(8) 0.1131(8) 0.045(3) Uani 1 1 d . . . H18A H 1.0650 0.0461 0.1519 0.080 Uiso 1 1 calc R . . H18B H 1.1148 0.1429 0.0849 0.080 Uiso 1 1 calc R . . H18C H 0.9745 0.1395 0.0585 0.080 Uiso 1 1 calc R . . N10 N 0.2303(14) 0.0056(12) 0.4131(12) 0.110(5) Uani 1 1 d . . . C19 C 0.2908(14) -0.0088(11) 0.3544(12) 0.065(4) Uani 1 1 d . . . C20 C 0.3722(12) -0.0281(9) 0.2748(10) 0.069(4) Uani 1 1 d . . . H20A H 0.3771 0.0399 0.2266 0.080 Uiso 1 1 calc R . . H20B H 0.3347 -0.0641 0.2401 0.080 Uiso 1 1 calc R . . H20C H 0.4583 -0.0728 0.3056 0.080 Uiso 1 1 calc R . . N11A N 0.686(3) 0.084(3) 0.169(3) 0.184(17) Uiso 0.67(2) 1 d PD A 1 C21A C 0.762(3) 0.007(3) 0.154(3) 0.149(16) Uiso 0.67(2) 1 d PD A 1 C22A C 0.7726(17) -0.0613(13) 0.1035(13) 0.049(5) Uiso 0.67(2) 1 d PD A 1 H22A H 0.7807 -0.1328 0.1515 0.080 Uiso 0.67(2) 1 calc PR A 1 H22B H 0.8485 -0.0624 0.0667 0.080 Uiso 0.67(2) 1 calc PR A 1 H22C H 0.6963 -0.0375 0.0562 0.080 Uiso 0.67(2) 1 calc PR A 1 N11B N 0.710(3) 0.105(2) 0.169(2) 0.034(8) Uiso 0.33(2) 1 d PD A 2 C21B C 0.724(3) 0.034(2) 0.1317(19) 0.013(6) Uiso 0.33(2) 1 d PD A 2 C22B C 0.660(5) -0.007(4) 0.081(4) 0.12(2) Uiso 0.33(2) 1 d PD A 2 H22D H 0.6383 -0.0675 0.1284 0.080 Uiso 0.33(2) 1 calc PR A 2 H22E H 0.7146 -0.0294 0.0333 0.080 Uiso 0.33(2) 1 calc PR A 2 H22F H 0.5817 0.0480 0.0440 0.080 Uiso 0.33(2) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Tm 0.0193(2) 0.01885(19) 0.0187(2) -0.00429(15) 0.00131(14) -0.00670(14) I1 0.0347(4) 0.0403(4) 0.0297(4) -0.0068(3) 0.0048(3) -0.0065(3) I2 0.0378(4) 0.0227(3) 0.0445(4) -0.0103(3) -0.0036(3) -0.0073(3) I3 0.0344(4) 0.0579(5) 0.0378(4) -0.0217(3) -0.0032(3) -0.0050(3) N1 0.025(4) 0.016(3) 0.020(4) -0.003(3) -0.001(3) -0.003(3) N2 0.019(4) 0.032(4) 0.015(4) -0.007(3) 0.005(3) -0.006(3) N3 0.026(4) 0.017(4) 0.019(4) -0.001(3) 0.000(3) -0.008(3) N4 0.027(4) 0.034(4) 0.023(4) -0.007(3) 0.003(3) -0.013(3) N5 0.031(4) 0.032(4) 0.028(4) -0.004(4) 0.000(3) -0.014(3) N6 0.043(5) 0.037(5) 0.024(4) -0.013(4) 0.008(3) -0.021(4) N7 0.018(4) 0.031(4) 0.028(4) -0.005(3) 0.000(3) 0.002(3) N8 0.020(4) 0.023(4) 0.026(4) -0.004(3) -0.003(3) -0.002(3) N9 0.027(4) 0.024(4) 0.039(5) -0.013(4) -0.002(3) -0.010(3) C1 0.019(4) 0.024(4) 0.023(4) -0.008(4) 0.002(3) -0.016(3) C2 0.025(5) 0.048(6) 0.038(6) -0.017(5) 0.006(4) -0.024(4) C3 0.020(5) 0.026(5) 0.027(5) -0.008(4) -0.002(4) -0.008(4) C4 0.035(6) 0.051(6) 0.036(6) -0.021(5) 0.009(4) -0.027(5) C5 0.022(5) 0.022(4) 0.025(5) -0.010(4) 0.009(4) -0.009(4) C6 0.037(5) 0.025(5) 0.028(5) -0.004(4) 0.011(4) -0.013(4) C7 0.018(5) 0.029(5) 0.029(5) -0.005(4) 0.000(4) -0.006(4) C8 0.026(5) 0.066(7) 0.029(5) -0.016(5) 0.006(4) -0.016(5) C9 0.039(6) 0.040(6) 0.029(6) -0.001(5) 0.001(4) -0.016(5) C10 0.074(9) 0.049(7) 0.046(7) 0.011(6) -0.018(6) -0.014(6) C11 0.036(6) 0.040(6) 0.024(5) -0.017(4) 0.003(4) -0.018(5) C12 0.049(7) 0.042(6) 0.058(7) -0.018(5) 0.001(5) -0.030(5) C13 0.021(5) 0.043(6) 0.031(5) -0.016(5) 0.002(4) -0.014(4) C14 0.042(6) 0.032(5) 0.042(6) -0.014(5) 0.005(5) -0.006(4) C15 0.017(5) 0.037(5) 0.028(5) -0.009(4) -0.001(4) -0.005(4) C16 0.022(5) 0.088(8) 0.038(6) -0.042(6) -0.003(4) -0.009(5) C17 0.022(5) 0.024(5) 0.040(6) -0.007(4) -0.006(4) -0.010(4) C18 0.047(7) 0.032(6) 0.055(7) -0.017(5) 0.006(5) -0.010(5) N10 0.082(11) 0.110(12) 0.116(14) -0.034(10) 0.001(9) -0.003(9) C19 0.057(9) 0.052(8) 0.073(11) -0.017(7) -0.025(7) 0.001(7) C20 0.076(9) 0.034(6) 0.086(10) -0.019(7) -0.033(8) -0.002(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 Tm N9 2.419(8) . ? Tm N3 2.431(6) . ? Tm N2 2.434(7) . ? Tm N5 2.440(7) . ? Tm N6 2.469(8) . ? Tm N7 2.478(7) . ? Tm N1 2.493(6) . ? Tm N8 2.508(8) . ? Tm N4 2.519(7) . ? N1 C1 1.493(10) . ? N2 C3 1.267(10) . ? N3 C5 1.262(10) . ? N4 C7 1.102(10) . ? N5 C9 1.152(11) . ? N6 C11 1.129(11) . ? N7 C13 1.134(11) . ? N8 C15 1.114(11) . ? N9 C17 1.143(11) . ? C1 C2 1.525(11) . ? C1 C5 1.537(11) . ? C1 C3 1.540(12) . ? C3 C4 1.494(12) . ? C5 C6 1.511(10) . ? C7 C8 1.488(12) . ? C9 C10 1.423(13) . ? C11 C12 1.485(12) . ? C13 C14 1.473(13) . ? C15 C16 1.455(13) . ? C17 C18 1.452(14) . ? N10 C19 1.084(17) . ? C19 C20 1.463(18) . ? N11A C21A 1.23(2) . ? C21A C22A 1.34(3) . ? N11B C21B 1.23(2) . ? C21B C22B 1.34(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N9 Tm N3 84.9(2) . . ? N9 Tm N2 136.5(2) . . ? N3 Tm N2 75.0(2) . . ? N9 Tm N5 77.7(3) . . ? N3 Tm N5 135.6(2) . . ? N2 Tm N5 90.2(2) . . ? N9 Tm N6 76.9(2) . . ? N3 Tm N6 139.7(2) . . ? N2 Tm N6 140.3(2) . . ? N5 Tm N6 75.1(2) . . ? N9 Tm N7 137.3(3) . . ? N3 Tm N7 73.7(2) . . ? N2 Tm N7 73.0(2) . . ? N5 Tm N7 141.9(2) . . ? N6 Tm N7 96.1(2) . . ? N9 Tm N1 73.0(2) . . ? N3 Tm N1 64.5(2) . . ? N2 Tm N1 63.6(2) . . ? N5 Tm N1 71.3(2) . . ? N6 Tm N1 138.6(2) . . ? N7 Tm N1 125.3(2) . . ? N9 Tm N8 68.4(2) . . ? N3 Tm N8 71.7(2) . . ? N2 Tm N8 135.4(2) . . ? N5 Tm N8 134.4(2) . . ? N6 Tm N8 68.3(2) . . ? N7 Tm N8 69.9(2) . . ? N1 Tm N8 123.0(2) . . ? N9 Tm N4 137.9(2) . . ? N3 Tm N4 137.2(2) . . ? N2 Tm N4 71.8(2) . . ? N5 Tm N4 71.0(2) . . ? N6 Tm N4 68.5(2) . . ? N7 Tm N4 71.3(2) . . ? N1 Tm N4 120.1(2) . . ? N8 Tm N4 116.7(2) . . ? C1 N1 Tm 107.0(4) . . ? C3 N2 Tm 120.6(6) . . ? C5 N3 Tm 119.6(5) . . ? C7 N4 Tm 173.6(7) . . ? C9 N5 Tm 177.2(8) . . ? C11 N6 Tm 176.2(8) . . ? C13 N7 Tm 159.2(7) . . ? C15 N8 Tm 171.2(7) . . ? C17 N9 Tm 166.1(7) . . ? N1 C1 C2 113.5(7) . . ? N1 C1 C5 104.7(6) . . ? C2 C1 C5 114.6(7) . . ? N1 C1 C3 104.2(6) . . ? C2 C1 C3 114.0(7) . . ? C5 C1 C3 104.7(6) . . ? N2 C3 C4 124.7(8) . . ? N2 C3 C1 115.8(8) . . ? C4 C3 C1 119.5(7) . . ? N3 C5 C6 123.2(8) . . ? N3 C5 C1 117.3(7) . . ? C6 C5 C1 119.4(7) . . ? N4 C7 C8 179.6(10) . . ? N5 C9 C10 179.4(12) . . ? N6 C11 C12 178.7(11) . . ? N7 C13 C14 177.6(10) . . ? N8 C15 C16 178.5(10) . . ? N9 C17 C18 178.0(10) . . ? N10 C19 C20 180(2) . . ? N11A C21A C22A 143(3) . . ? N11B C21B C22B 143(3) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.931 _refine_diff_density_min -1.521 _refine_diff_density_rms 0.211 #===END