data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Liviu Mirica' _publ_contact_author_email mirica@wustl.edu loop_ _publ_author_name 'Fengzhi Tang' 'Fengrui Qu' 'Julia Khusnutdinova' 'Nigam Rath' 'Liviu Mirica' data_l26410 _database_code_depnum_ccdc_archive 'CCDC 884994' #TrackingRef 'CombinedCIFsDaltonUpdated.cif' _audit_creation_method SHELXL-2012 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H23 Cl N4 Pd, Cl O4, C2 H3 N' _chemical_formula_sum 'C19 H26 Cl2 N5 O4 Pd' _chemical_formula_weight 565.75 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' 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' _space_group_crystal_system orthorhombic _space_group_IT_number 62 _space_group_name_H-M_alt 'P n m a' _space_group_name_Hall '-P 2ac 2n' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_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 13.6407(8) _cell_length_b 9.5515(5) _cell_length_c 17.0852(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2226.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9871 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 32.75 _exptl_crystal_description rectangular _exptl_crystal_colour purple _exptl_crystal_density_meas no _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.688 _exptl_crystal_F_000 1148 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.217 _exptl_crystal_size_mid 0.153 _exptl_crystal_size_min 0.138 _exptl_absorpt_coefficient_mu 1.110 _shelx_estimated_absorpt_T_min 0.795 _shelx_estimated_absorpt_T_max 0.862 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7946 _exptl_absorpt_correction_T_max 0.8619 _exptl_absorpt_process_details 'sadabs v2008/1' _exptl_special_details ; All H atoms were added in their calculated positions and were treated using appropriate riding models. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 41610 _diffrn_reflns_sigmaI/netI 0.0252 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.910 _diffrn_reflns_theta_max 32.752 _diffrn_reflns_theta_full 25.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 4309 _reflns_number_gt 3838 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; The reflections were merged according to the crystal class for structure refinement and the calculation of statistics. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2012 (Sheldrick, 2012)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; All H atoms were added in their calculated positions and were treated using appropriate riding models. The Me group and the Cl bonded to the Pd atom are disorderd over the two sites and were refined as 50% occupancy atoms. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0103P)^2^+7.1000P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 4309 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0892 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.272 _refine_ls_restrained_S_all 1.272 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.684310(18) 0.2500 0.538844(15) 0.01051(6) Uani 1 2 d SD . . Cl1 Cl 0.6103(2) 0.0852(4) 0.4562(2) 0.0203(4) Uani 0.5 1 d PD A 1 C1 C 0.6320(9) 0.0980(16) 0.4679(8) 0.021(2) Uani 0.5 1 d PD A 2 H1A H 0.6739 0.0904 0.4215 0.031 Uiso 0.5 1 calc PRD A 2 H1B H 0.5651 0.1214 0.4518 0.031 Uiso 0.5 1 calc PRD A 2 H1C H 0.6318 0.0086 0.4960 0.031 Uiso 0.5 1 calc PRD A 2 N1 N 0.74995(15) 0.1075(2) 0.61515(12) 0.0123(4) Uani 1 1 d D A . N3 N 0.8433(2) 0.2500 0.49377(17) 0.0140(5) Uani 1 2 d SD A . N4 N 0.5751(2) 0.2500 0.64437(18) 0.0131(5) Uani 1 2 d SD A . C2 C 0.70546(17) 0.0804(3) 0.68328(15) 0.0155(4) Uani 1 1 d D . . C3 C 0.7550(2) 0.0123(3) 0.74288(17) 0.0207(5) Uani 1 1 d D A . H3A H 0.7234 -0.0065 0.7913 0.025 Uiso 1 1 calc RD . . C4 C 0.8515(2) -0.0279(3) 0.73057(17) 0.0205(5) Uani 1 1 d D . . H4A H 0.8858 -0.0790 0.7697 0.025 Uiso 1 1 calc RD A . C5 C 0.89753(19) 0.0067(3) 0.66110(16) 0.0182(5) Uani 1 1 d D A . H5A H 0.9642 -0.0178 0.6526 0.022 Uiso 1 1 calc RD . . C6 C 0.84503(18) 0.0775(3) 0.60414(15) 0.0143(4) Uani 1 1 d D . . C7 C 0.88690(19) 0.1199(3) 0.52639(15) 0.0190(5) Uani 1 1 d D A . H7A H 0.9585 0.1336 0.5322 0.023 Uiso 1 1 calc RD . . H7B H 0.8766 0.0427 0.4886 0.023 Uiso 1 1 calc RD . . C8 C 0.59879(18) 0.1212(3) 0.68829(17) 0.0188(5) Uani 1 1 d D A . H8A H 0.5583 0.0434 0.6678 0.023 Uiso 1 1 calc RD . . H8B H 0.5811 0.1350 0.7440 0.023 Uiso 1 1 calc RD . . C9 C 0.8552(3) 0.2500 0.4083(2) 0.0218(8) Uani 1 2 d SD . . H9A H 0.9238 0.2500 0.3957 0.033 Uiso 1 2 d SRD A . H9B H 0.8249 0.1679 0.3867 0.033 Uiso 1 1 d RD . . C10 C 0.4696(3) 0.2500 0.6250(2) 0.0179(7) Uani 1 2 d SD . . H10A H 0.4311 0.2500 0.6721 0.027 Uiso 1 2 d SRD A . H10B H 0.4546 0.3321 0.5949 0.027 Uiso 1 1 d RD . . Cl2 Cl 0.84160(6) 0.7500 0.42400(5) 0.02066(18) Uani 1 2 d SD . . O1 O 0.8679(2) 0.7500 0.50550(18) 0.0311(7) Uani 1 2 d SD . . O2 O 0.7381(2) 0.7500 0.4150(2) 0.0435(10) Uani 1 2 d SD . . O3 O 0.88280(18) 0.8722(3) 0.38712(13) 0.0327(5) Uani 1 1 d D . . N1S N 0.4456(3) 0.2500 0.2763(2) 0.0290(8) Uani 1 2 d SD . . C1S C 0.4088(3) 0.2500 0.3364(3) 0.0217(8) Uani 1 2 d SD . . C2S C 0.3612(4) 0.2500 0.4121(3) 0.0301(10) Uani 1 2 d SD . . H2S1 H 0.2922 0.2764 0.4058 0.045 Uiso 0.5 1 calc PRD B -1 H2S2 H 0.3938 0.3174 0.4466 0.045 Uiso 0.5 1 calc PRD B -1 H2S3 H 0.3652 0.1562 0.4351 0.045 Uiso 0.5 1 calc PRD B -1 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 Pd1 0.01021(10) 0.00981(10) 0.01149(11) 0.000 -0.00134(9) 0.000 Cl1 0.0197(12) 0.0171(9) 0.0242(10) -0.0066(7) -0.0050(8) -0.0035(8) C1 0.016(5) 0.020(4) 0.027(6) -0.007(3) 0.000(3) -0.007(3) N1 0.0122(8) 0.0099(8) 0.0148(9) -0.0001(7) -0.0008(7) 0.0018(7) N3 0.0155(12) 0.0172(14) 0.0094(12) 0.000 0.0017(10) 0.000 N4 0.0108(11) 0.0114(12) 0.0170(14) 0.000 -0.0008(10) 0.000 C2 0.0139(10) 0.0140(10) 0.0186(11) 0.0039(9) 0.0015(8) 0.0011(8) C3 0.0176(11) 0.0229(13) 0.0215(12) 0.0090(11) 0.0033(10) 0.0033(10) C4 0.0172(11) 0.0222(13) 0.0222(13) 0.0070(11) -0.0023(9) 0.0030(10) C5 0.0152(10) 0.0192(12) 0.0203(12) 0.0022(10) -0.0008(9) 0.0036(9) C6 0.0125(9) 0.0145(10) 0.0160(11) -0.0008(9) 0.0001(8) 0.0009(8) C7 0.0179(11) 0.0234(13) 0.0156(12) 0.0017(10) 0.0033(9) 0.0075(10) C8 0.0126(10) 0.0201(12) 0.0238(13) 0.0088(10) 0.0042(9) 0.0021(9) C9 0.0269(19) 0.028(2) 0.0101(15) 0.000 0.0038(14) 0.000 C10 0.0109(14) 0.0214(17) 0.0213(18) 0.000 -0.0014(12) 0.000 Cl2 0.0119(3) 0.0345(5) 0.0155(4) 0.000 -0.0007(3) 0.000 O1 0.0276(16) 0.052(2) 0.0139(13) 0.000 -0.0007(12) 0.000 O2 0.0120(13) 0.079(3) 0.040(2) 0.000 -0.0025(13) 0.000 O3 0.0356(12) 0.0393(14) 0.0233(11) 0.0043(10) -0.0017(9) -0.0072(11) N1S 0.0258(18) 0.035(2) 0.0268(19) 0.000 0.0021(15) 0.000 C1S 0.0193(17) 0.0197(18) 0.026(2) 0.000 -0.0005(15) 0.000 C2S 0.037(2) 0.031(2) 0.022(2) 0.000 0.0071(18) 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 Pd1 C1 2.021(11) 7_565 ? Pd1 C1 2.021(11) . ? Pd1 N1 2.086(2) . ? Pd1 N1 2.087(2) 7_565 ? Pd1 N3 2.301(3) . ? Pd1 N4 2.339(3) . ? Pd1 Cl1 2.343(3) . ? Pd1 Cl1 2.343(3) 7_565 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? N1 C2 1.338(3) . ? N1 C6 1.342(3) . ? N3 C9 1.468(5) . ? N3 C7 1.486(3) 7_565 ? N3 C7 1.486(3) . ? N4 C8 1.477(3) . ? N4 C8 1.477(3) 7_565 ? N4 C10 1.477(4) . ? C2 C3 1.384(4) . ? C2 C8 1.509(3) . ? C3 C4 1.388(4) . ? C3 H3A 0.9500 . ? C4 C5 1.383(4) . ? C4 H4A 0.9500 . ? C5 C6 1.385(4) . ? C5 H5A 0.9500 . ? C6 C7 1.502(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9602 . ? C9 H9B 0.9600 . ? C10 H10A 0.9601 . ? C10 H10B 0.9599 . ? Cl2 O2 1.420(3) . ? Cl2 O1 1.438(3) . ? Cl2 O3 1.440(3) 7_575 ? Cl2 O3 1.440(3) . ? N1S C1S 1.143(6) . ? C1S C2S 1.448(6) . ? C2S H2S1 0.9800 . ? C2S H2S2 0.9800 . ? C2S H2S3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pd1 C1 91.8(9) 7_565 . ? C1 Pd1 N1 174.0(4) 7_565 . ? C1 Pd1 N1 93.3(5) . . ? C1 Pd1 N1 93.3(5) 7_565 7_565 ? C1 Pd1 N1 174.0(4) . 7_565 ? N1 Pd1 N1 81.42(11) . 7_565 ? C1 Pd1 N3 97.6(4) 7_565 . ? C1 Pd1 N3 97.6(4) . . ? N1 Pd1 N3 78.74(8) . . ? N1 Pd1 N3 78.74(8) 7_565 . ? C1 Pd1 N4 103.8(4) 7_565 . ? C1 Pd1 N4 103.8(4) . . ? N1 Pd1 N4 77.97(8) . . ? N1 Pd1 N4 77.97(8) 7_565 . ? N3 Pd1 N4 149.12(10) . . ? N1 Pd1 Cl1 97.09(11) . . ? N1 Pd1 Cl1 178.32(11) 7_565 . ? N3 Pd1 Cl1 101.78(10) . . ? N4 Pd1 Cl1 100.98(11) . . ? N1 Pd1 Cl1 178.32(11) . 7_565 ? N1 Pd1 Cl1 97.09(11) 7_565 7_565 ? N3 Pd1 Cl1 101.78(10) . 7_565 ? N4 Pd1 Cl1 100.98(11) . 7_565 ? Cl1 Pd1 Cl1 84.38(18) . 7_565 ? Pd1 C1 H1A 109.5 . . ? Pd1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Pd1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 N1 C6 121.3(2) . . ? C2 N1 Pd1 118.39(16) . . ? C6 N1 Pd1 117.81(17) . . ? C9 N3 C7 109.17(18) . 7_565 ? C9 N3 C7 109.17(18) . . ? C7 N3 C7 113.5(3) 7_565 . ? C9 N3 Pd1 115.9(2) . . ? C7 N3 Pd1 104.58(16) 7_565 . ? C7 N3 Pd1 104.58(16) . . ? C8 N4 C8 112.8(3) . 7_565 ? C8 N4 C10 109.08(18) . . ? C8 N4 C10 109.08(18) 7_565 . ? C8 N4 Pd1 104.61(16) . . ? C8 N4 Pd1 104.61(16) 7_565 . ? C10 N4 Pd1 116.7(2) . . ? N1 C2 C3 120.7(2) . . ? N1 C2 C8 115.9(2) . . ? C3 C2 C8 123.4(2) . . ? C2 C3 C4 118.8(3) . . ? C2 C3 H3A 120.6 . . ? C4 C3 H3A 120.6 . . ? C5 C4 C3 119.6(2) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C6 119.0(2) . . ? C4 C5 H5A 120.5 . . ? C6 C5 H5A 120.5 . . ? N1 C6 C5 120.4(2) . . ? N1 C6 C7 115.7(2) . . ? C5 C6 C7 123.8(2) . . ? N3 C7 C6 113.9(2) . . ? N3 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? N3 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? N4 C8 C2 113.4(2) . . ? N4 C8 H8A 108.9 . . ? C2 C8 H8A 108.9 . . ? N4 C8 H8B 108.9 . . ? C2 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? N3 C9 H9A 109.3 . . ? N3 C9 H9B 109.6 . . ? H9A C9 H9B 109.5 . . ? N4 C10 H10A 110.2 . . ? N4 C10 H10B 109.1 . . ? H10A C10 H10B 109.5 . . ? O2 Cl2 O1 110.7(2) . . ? O2 Cl2 O3 109.90(13) . 7_575 ? O1 Cl2 O3 109.05(12) . 7_575 ? O2 Cl2 O3 109.90(13) . . ? O1 Cl2 O3 109.05(12) . . ? O3 Cl2 O3 108.2(2) 7_575 . ? N1S C1S C2S 179.5(5) . . ? C1S C2S H2S1 109.5 . . ? C1S C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? C1S C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 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 C6 N1 C2 C3 -4.0(4) . . . . ? Pd1 N1 C2 C3 -165.6(2) . . . . ? C6 N1 C2 C8 179.1(2) . . . . ? Pd1 N1 C2 C8 17.6(3) . . . . ? N1 C2 C3 C4 -0.3(4) . . . . ? C8 C2 C3 C4 176.2(3) . . . . ? C2 C3 C4 C5 3.2(4) . . . . ? C3 C4 C5 C6 -1.9(4) . . . . ? C2 N1 C6 C5 5.4(4) . . . . ? Pd1 N1 C6 C5 167.1(2) . . . . ? C2 N1 C6 C7 -177.1(2) . . . . ? Pd1 N1 C6 C7 -15.4(3) . . . . ? C4 C5 C6 N1 -2.4(4) . . . . ? C4 C5 C6 C7 -179.7(3) . . . . ? C9 N3 C7 C6 -155.9(3) . . . . ? C7 N3 C7 C6 82.1(3) 7_565 . . . ? Pd1 N3 C7 C6 -31.3(3) . . . . ? N1 C6 C7 N3 33.2(3) . . . . ? C5 C6 C7 N3 -149.4(3) . . . . ? C8 N4 C8 C2 -81.8(3) 7_565 . . . ? C10 N4 C8 C2 156.8(3) . . . . ? Pd1 N4 C8 C2 31.4(3) . . . . ? N1 C2 C8 N4 -34.8(3) . . . . ? C3 C2 C8 N4 148.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C7 H7A O3 0.99 2.57 3.473(4) 152.0 5_766 C7 H7B O3 0.99 2.38 3.356(4) 168.4 1_545 C8 H8B O3 0.99 2.50 3.407(4) 152.9 2_665 _refine_diff_density_max 0.675 _refine_diff_density_min -1.368 _refine_diff_density_rms 0.120