#============================================================================== data_global #============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Michael W. Day Beckman Institute California Institute of Technology Pasadena, CA 91125 USA ; _publ_contact_author_phone '(818) 395 2734' _publ_contact_author_fax '(818) 449 4159' _publ_contact_author_email mikeday@caltech.edu _publ_requested_journal ? _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for deposition in the Cambridge Structural Database. ; #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Day, Michael W.' #<--'Last name, first name' ; Beckman Institute California Institute of Technology Pasadena, CA 91125 USA ; 'Trend, Raissa M.' ; Division of Chemistry and Chemical Engineering California Institute of Technology Pasadena, CA 91125 USA ; 'Stoltz, Brian M.' ; Division of Chemistry and Chemical Engineering California Institute of Technology Pasadena, CA 91125 USA ; #============================================================================== # 4. TEXT _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_references ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #============================================================================== # If more than one structure is reported, sections 5-10 should be filled in # per structure. For each data set, replace the '?' in the data_? line below # by a unique identifier. #============================================================================== # 5. CHEMICAL DATA data_rmt08 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H26 Cl2 N2 Pd' _chemical_formula_weight 411.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 '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' 'Pd' 'Pd' -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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' _cell_length_a 9.2815(3) _cell_length_b 11.4873(4) _cell_length_c 15.1073(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1610.73(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 24049 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 44.96 _exptl_crystal_description Fragment _exptl_crystal_colour Maroon _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 1.476 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.5968 _exptl_absorpt_correction_T_max 0.7372 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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' _diffrn_measurement_method '\w scans at 7 \f settings' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44470 _diffrn_reflns_av_R_equivalents 0.0673 _diffrn_reflns_av_sigmaI/netI 0.0629 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 44.97 _reflns_number_total 11830 _reflns_number_gt 9732 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART v5.054' _computing_cell_refinement 'Bruker SAINT v6.45' _computing_data_reduction 'Bruker SAINT v6.45' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.042(13) _refine_ls_number_reflns 11830 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0542 _refine_ls_wR_factor_gt 0.0525 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _refine_ls_shift/su_max 0.004 _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 Pd Pd 0.807355(11) 0.958095(8) 0.989923(6) 0.00925(2) Uani 1 1 d . . . Cl1 Cl 0.59135(4) 1.02257(4) 1.05092(2) 0.02492(10) Uani 1 1 d . . . Cl2 Cl 0.82253(5) 0.83520(3) 1.11093(2) 0.01728(7) Uani 1 1 d . . . N1 N 0.77120(12) 1.03490(11) 0.86508(7) 0.0103(2) Uani 1 1 d . . . N2 N 1.02754(13) 0.94251(11) 0.95270(7) 0.0108(2) Uani 1 1 d . . . C1 C 0.61551(16) 1.06523(15) 0.84683(10) 0.0158(3) Uani 1 1 d . . . C2 C 0.51710(17) 0.95932(18) 0.84100(10) 0.0202(3) Uani 1 1 d . . . C3 C 0.57084(18) 0.86868(16) 0.77566(11) 0.0199(3) Uani 1 1 d . . . C4 C 0.72877(18) 0.84209(14) 0.79420(10) 0.0164(3) Uani 1 1 d . . . C5 C 0.81647(15) 0.95399(13) 0.79086(7) 0.0110(2) Uani 1 1 d . . . C6 C 0.97990(16) 0.93452(14) 0.78876(9) 0.0144(3) Uani 1 1 d . . . C7 C 1.04124(18) 0.87300(14) 0.86909(10) 0.0152(3) Uani 1 1 d . . . C8 C 1.12395(17) 0.88514(13) 1.02015(10) 0.0155(3) Uani 1 1 d . . . C9 C 1.14214(17) 0.95313(15) 1.10582(10) 0.0170(3) Uani 1 1 d . . . C10 C 1.18511(18) 1.07919(13) 1.09069(9) 0.0153(2) Uani 1 1 d . . . C11 C 1.08428(17) 1.13430(13) 1.02298(9) 0.0135(3) Uani 1 1 d . . . C12 C 1.08682(16) 1.06392(12) 0.93762(9) 0.0122(3) Uani 1 1 d . . . C13 C 1.01858(17) 1.12383(14) 0.85750(10) 0.0146(3) Uani 1 1 d . . . C14 C 0.85656(17) 1.14497(13) 0.86180(10) 0.0140(3) Uani 1 1 d . . . C15 C 1.05326(17) 1.05184(16) 0.77526(9) 0.0177(3) Uani 1 1 d . . . H1A H 0.6125(18) 1.1041(15) 0.7962(12) 0.008(4) Uiso 1 1 d . . . H1B H 0.5881(19) 1.1156(16) 0.8888(12) 0.011(4) Uiso 1 1 d . . . H2A H 0.501(2) 0.9255(17) 0.8965(13) 0.019(5) Uiso 1 1 d . . . H2B H 0.424(3) 0.982(2) 0.8218(15) 0.041(7) Uiso 1 1 d . . . H3A H 0.563(2) 0.8972(17) 0.7163(14) 0.021(5) Uiso 1 1 d . . . H3B H 0.516(2) 0.7969(18) 0.7759(13) 0.024(6) Uiso 1 1 d . . . H4A H 0.743(2) 0.807(2) 0.8417(16) 0.036(6) Uiso 1 1 d . . . H4B H 0.771(2) 0.7889(16) 0.7526(12) 0.017(5) Uiso 1 1 d . . . H5 H 0.7923(16) 0.9932(14) 0.7342(9) 0.001(3) Uiso 1 1 d . . . H6 H 1.0032(19) 0.8877(15) 0.7388(11) 0.005(4) Uiso 1 1 d . . . H7A H 0.9934(19) 0.8034(15) 0.8808(11) 0.005(4) Uiso 1 1 d . . . H7B H 1.138(2) 0.8605(17) 0.8610(12) 0.012(5) Uiso 1 1 d . . . H8A H 1.2193(17) 0.8821(13) 0.9967(12) 0.008(4) Uiso 1 1 d . . . H8B H 1.085(2) 0.8096(16) 1.0326(11) 0.011(4) Uiso 1 1 d . . . H9A H 1.057(2) 0.9404(15) 1.1344(12) 0.010(4) Uiso 1 1 d . . . H9B H 1.216(2) 0.9152(18) 1.1427(14) 0.026(5) Uiso 1 1 d . . . H10A H 1.275(2) 1.0858(18) 1.0694(13) 0.024(5) Uiso 1 1 d . . . H10B H 1.183(2) 1.1254(16) 1.1435(13) 0.019(5) Uiso 1 1 d . . . H11A H 0.985(2) 1.1406(17) 1.0455(12) 0.016(5) Uiso 1 1 d . . . H11B H 1.1154(17) 1.2089(14) 1.0097(12) 0.007(4) Uiso 1 1 d . . . H12 H 1.193(2) 1.0520(16) 0.9273(12) 0.020(5) Uiso 1 1 d . . . H13 H 1.0570(19) 1.2003(16) 0.8563(12) 0.009(4) Uiso 1 1 d . . . H14A H 0.822(2) 1.1979(16) 0.9101(12) 0.015(4) Uiso 1 1 d . . . H14B H 0.816(2) 1.1883(16) 0.8072(12) 0.015(4) Uiso 1 1 d . . . H15A H 1.018(2) 1.0886(16) 0.7263(12) 0.011(4) Uiso 1 1 d . . . H15B H 1.159(2) 1.038(2) 0.7697(13) 0.026(5) 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 Pd 0.01059(4) 0.01118(4) 0.00600(3) 0.00111(3) 0.00025(3) -0.00072(4) Cl1 0.01660(17) 0.0475(3) 0.01072(15) 0.00276(15) 0.00525(12) 0.00745(17) Cl2 0.0272(2) 0.01511(16) 0.00952(13) 0.00376(10) -0.00394(13) -0.00702(14) N1 0.0104(5) 0.0136(5) 0.0070(4) 0.0008(4) 0.0009(3) 0.0024(4) N2 0.0127(5) 0.0104(6) 0.0092(5) -0.0018(3) -0.0016(4) 0.0016(4) C1 0.0121(7) 0.0251(9) 0.0102(6) 0.0011(5) 0.0000(4) 0.0073(5) C2 0.0121(7) 0.0343(9) 0.0143(6) 0.0023(7) -0.0008(5) -0.0008(7) C3 0.0188(8) 0.0272(9) 0.0137(7) -0.0003(6) -0.0021(5) -0.0071(7) C4 0.0217(8) 0.0158(7) 0.0116(6) -0.0008(5) -0.0022(5) -0.0028(5) C5 0.0130(5) 0.0131(5) 0.0070(4) -0.0011(4) 0.0002(4) 0.0024(6) C6 0.0128(6) 0.0208(8) 0.0094(6) -0.0045(5) 0.0011(4) 0.0043(5) C7 0.0153(7) 0.0157(7) 0.0144(6) -0.0060(5) -0.0013(5) 0.0058(5) C8 0.0163(7) 0.0139(7) 0.0163(7) -0.0022(5) -0.0062(5) 0.0037(5) C9 0.0199(7) 0.0152(7) 0.0159(6) -0.0009(6) -0.0070(5) 0.0002(6) C10 0.0125(6) 0.0191(7) 0.0143(6) -0.0033(5) -0.0012(5) -0.0034(6) C11 0.0153(6) 0.0119(6) 0.0132(6) -0.0014(5) -0.0002(5) -0.0026(5) C12 0.0100(6) 0.0147(7) 0.0120(6) -0.0009(4) 0.0011(4) -0.0017(5) C13 0.0161(7) 0.0164(7) 0.0115(6) 0.0024(5) 0.0011(5) -0.0044(5) C14 0.0189(7) 0.0107(6) 0.0124(6) 0.0019(5) 0.0014(5) 0.0010(5) C15 0.0160(7) 0.0267(8) 0.0104(6) 0.0006(6) 0.0040(5) -0.0027(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 Pd N1 2.1091(11) . yes Pd N2 2.1271(12) . yes Pd Cl2 2.3140(3) . yes Pd Cl1 2.3275(4) . yes N1 C14 1.493(2) . ? N1 C1 1.5118(18) . ? N1 C5 1.5158(17) . ? N2 C7 1.4998(18) . ? N2 C8 1.5078(18) . ? N2 C12 1.5166(19) . ? C1 C2 1.524(2) . ? C1 H1A 0.886(18) . ? C1 H1B 0.896(18) . ? C2 C3 1.519(2) . ? C2 H2A 0.94(2) . ? C2 H2B 0.95(2) . ? C3 C4 1.523(2) . ? C3 H3A 0.96(2) . ? C3 H3B 0.97(2) . ? C4 C5 1.522(2) . ? C4 H4A 0.83(2) . ? C4 H4B 0.960(18) . ? C5 C6 1.534(2) . ? C5 H5 0.993(15) . ? C6 C7 1.515(2) . ? C6 C15 1.524(2) . ? C6 H6 0.951(17) . ? C7 H7A 0.931(17) . ? C7 H7B 0.918(18) . ? C8 C9 1.521(2) . ? C8 H8A 0.954(16) . ? C8 H8B 0.960(18) . ? C9 C10 1.519(2) . ? C9 H9A 0.912(18) . ? C9 H9B 0.98(2) . ? C10 C11 1.524(2) . ? C10 H10A 0.90(2) . ? C10 H10B 0.958(19) . ? C11 C12 1.522(2) . ? C11 H11A 0.984(19) . ? C11 H11B 0.926(16) . ? C12 C13 1.530(2) . ? C12 H12 1.005(19) . ? C13 C14 1.525(2) . ? C13 C15 1.527(2) . ? C13 H13 0.948(18) . ? C14 H14A 1.002(18) . ? C14 H14B 1.035(18) . ? C15 H15A 0.914(19) . ? C15 H15B 1.00(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Pd N2 87.23(4) . . yes N1 Pd Cl2 166.25(4) . . yes N2 Pd Cl2 95.68(3) . . yes N1 Pd Cl1 94.81(3) . . yes N2 Pd Cl1 163.54(3) . . yes Cl2 Pd Cl1 86.205(15) . . yes C14 N1 C1 107.82(12) . . ? C14 N1 C5 110.34(11) . . ? C1 N1 C5 105.75(11) . . ? C14 N1 Pd 107.43(8) . . ? C1 N1 Pd 114.30(8) . . ? C5 N1 Pd 111.15(8) . . ? C7 N2 C8 106.63(11) . . ? C7 N2 C12 109.41(11) . . ? C8 N2 C12 106.75(11) . . ? C7 N2 Pd 110.42(9) . . ? C8 N2 Pd 115.36(9) . . ? C12 N2 Pd 108.11(8) . . ? N1 C1 C2 113.55(13) . . ? N1 C1 H1A 107.7(11) . . ? C2 C1 H1A 109.5(11) . . ? N1 C1 H1B 106.9(12) . . ? C2 C1 H1B 112.8(12) . . ? H1A C1 H1B 106.1(16) . . ? C3 C2 C1 112.83(13) . . ? C3 C2 H2A 110.5(12) . . ? C1 C2 H2A 111.9(12) . . ? C3 C2 H2B 106.9(14) . . ? C1 C2 H2B 110.0(15) . . ? H2A C2 H2B 104.1(18) . . ? C2 C3 C4 109.51(13) . . ? C2 C3 H3A 110.5(12) . . ? C4 C3 H3A 108.0(12) . . ? C2 C3 H3B 114.0(13) . . ? C4 C3 H3B 109.6(13) . . ? H3A C3 H3B 104.9(17) . . ? C5 C4 C3 109.83(13) . . ? C5 C4 H4A 110.6(16) . . ? C3 C4 H4A 113.9(16) . . ? C5 C4 H4B 107.3(12) . . ? C3 C4 H4B 113.6(12) . . ? H4A C4 H4B 101.3(19) . . ? N1 C5 C4 110.18(11) . . ? N1 C5 C6 112.27(11) . . ? C4 C5 C6 113.98(12) . . ? N1 C5 H5 107.3(9) . . ? C4 C5 H5 106.9(9) . . ? C6 C5 H5 105.8(9) . . ? C7 C6 C15 110.60(13) . . ? C7 C6 C5 115.02(12) . . ? C15 C6 C5 108.41(12) . . ? C7 C6 H6 106.6(11) . . ? C15 C6 H6 107.0(10) . . ? C5 C6 H6 108.9(11) . . ? N2 C7 C6 113.23(12) . . ? N2 C7 H7A 104.9(11) . . ? C6 C7 H7A 111.9(11) . . ? N2 C7 H7B 106.2(12) . . ? C6 C7 H7B 109.5(12) . . ? H7A C7 H7B 110.9(16) . . ? N2 C8 C9 114.61(12) . . ? N2 C8 H8A 108.4(10) . . ? C9 C8 H8A 103.4(10) . . ? N2 C8 H8B 107.5(11) . . ? C9 C8 H8B 109.8(10) . . ? H8A C8 H8B 113.2(14) . . ? C10 C9 C8 112.99(13) . . ? C10 C9 H9A 116.9(11) . . ? C8 C9 H9A 103.0(11) . . ? C10 C9 H9B 108.9(12) . . ? C8 C9 H9B 109.3(12) . . ? H9A C9 H9B 105.2(16) . . ? C9 C10 C11 109.62(12) . . ? C9 C10 H10A 112.2(13) . . ? C11 C10 H10A 107.2(13) . . ? C9 C10 H10B 113.3(12) . . ? C11 C10 H10B 108.3(12) . . ? H10A C10 H10B 105.9(17) . . ? C12 C11 C10 109.79(12) . . ? C12 C11 H11A 110.3(11) . . ? C10 C11 H11A 111.9(11) . . ? C12 C11 H11B 107.6(12) . . ? C10 C11 H11B 109.8(11) . . ? H11A C11 H11B 107.4(15) . . ? N2 C12 C11 110.83(11) . . ? N2 C12 C13 112.49(12) . . ? C11 C12 C13 115.15(12) . . ? N2 C12 H12 104.7(11) . . ? C11 C12 H12 102.6(11) . . ? C13 C12 H12 110.1(10) . . ? C14 C13 C15 109.20(13) . . ? C14 C13 C12 116.51(12) . . ? C15 C13 C12 108.23(13) . . ? C14 C13 H13 102.9(11) . . ? C15 C13 H13 114.0(11) . . ? C12 C13 H13 106.0(11) . . ? N1 C14 C13 112.95(12) . . ? N1 C14 H14A 108.7(11) . . ? C13 C14 H14A 116.2(11) . . ? N1 C14 H14B 103.8(10) . . ? C13 C14 H14B 113.9(11) . . ? H14A C14 H14B 99.9(14) . . ? C6 C15 C13 106.02(12) . . ? C6 C15 H15A 110.8(12) . . ? C13 C15 H15A 109.4(12) . . ? C6 C15 H15B 108.0(13) . . ? C13 C15 H15B 111.3(12) . . ? H15A C15 H15B 111.2(17) . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 44.97 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 1.557 _refine_diff_density_min -1.497 _refine_diff_density_rms 0.139