# 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 #TrackingRef 'structures_dalton2011.txt' #======================================================================= _publ_contact_author # Name and address of author ; Brenna, Stefano Dept of chemistry, Universita degli studi dell Insubria, Como 11-22100, ITaly ; _publ_contact_author_phone '+39 31 2386476' _publ_contact_author_fax '+39 31 2386119' _publ_contact_author_email stefano.brenna@uninsubria.it _publ_requested_coeditor_name ? _publ_requested_category ? _publ_contact_letter ; ; _publ_requested_letter ; ; #======================================================================= # 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_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 ; Ni(II) and Pd(II) pyridinyloxazolidine-compounds: synthesis, X-ray characterisation and catalytic activities in the aza-Michael reaction ; # 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 G.A.Ardizzoia ; Dept of chemistry, Universita degli studi dell Insubria, Como 11-22100, ITaly ; S.Brenna ; Dept of chemistry, Universita degli studi dell Insubria, Como 11-22100, ITaly ; B.Therrien ; Institut de Chimie, Universit\'e de Neuch\^atel, Service Analytique Facultaire, Ave de Bellevaux 51, CH-2000 Neuch\^atel, Switzerland ; #======================================================================= # 4. TEXT _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_references ; Sheldrick, G. M. (1990). "SHELXS-97 Program for Crystal Structure Determination", Acta Cryst., A46, 467-473. Sheldrick, G. M. (1997). SHELXL-97. Univ. of G\"ottingen, G\"ottingen, Germany. Stoe & Cie (2000). IPDS Software. Stoe & Cie GmbH, Darmstadt, Germany. Walker, N. & Stuart, D. (1983). Acta Cryst. A39, 158-166. ; _publ_section_acknowledgements ; ; _publ_contact_author_name 'Brenna, Stefano' data_d:complex1 _database_code_depnum_ccdc_archive 'CCDC 830383' #TrackingRef 'structures_dalton2011.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 Cl2 N2 O Pd' _chemical_formula_sum 'C14 H14 Cl2 N2 O Pd' _chemical_formula_weight 403.57 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' Cl Cl 0.1484 0.1585 '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' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6308(6) _cell_length_b 12.3692(6) _cell_length_c 15.1831(10) _cell_angle_alpha 90.00 _cell_angle_beta 114.683(5) _cell_angle_gamma 90.00 _cell_volume 1472.79(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 26.05 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.820 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 1.618 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.323 _exptl_absorpt_correction_T_max 0.754 _exptl_absorpt_process_details 'Walker, N. & Stuart, D. (1983)' _exptl_special_details ; A crystal was mounted at 173K on a Stoe Image Plate Diffraction System (Stoe & Cie, 2000) using MoK\a graphite monochromated radiation. Image plate distance 70mm, \f oscillation scans 0 - 200\%, step \D\f = 1.5\%, 3 minutes per frame. ; _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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 28038 _diffrn_reflns_av_R_equivalents 0.0902 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 29.18 _reflns_number_total 3971 _reflns_number_gt 3546 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe & Cie, 2000)' _computing_cell_refinement 'CELL (Stoe & Cie, 2000)' _computing_data_reduction 'INTEGRATE (Stoe & Cie, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-32 (Farrugia, 1997)' _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^)+(0.0000P)^2^+6.5491P] 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 3971 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1005 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.312 _refine_ls_restrained_S_all 1.312 _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 C1 C 0.7644(5) -0.0263(3) -0.0204(3) 0.0196(8) Uani 1 1 d . . . H1 H 0.7827 -0.0450 -0.0746 0.023 Uiso 1 1 calc R . . C2 C 0.7083(6) -0.1042(4) 0.0243(3) 0.0246(9) Uani 1 1 d . . . H2 H 0.6856 -0.1739 -0.0009 0.029 Uiso 1 1 calc R . . C3 C 0.6861(6) -0.0781(4) 0.1072(3) 0.0271(10) Uani 1 1 d . . . H3 H 0.6503 -0.1301 0.1389 0.033 Uiso 1 1 calc R . . C4 C 0.7183(6) 0.0274(4) 0.1419(3) 0.0247(9) Uani 1 1 d . . . H4 H 0.7053 0.0470 0.1975 0.030 Uiso 1 1 calc R . . C5 C 0.7696(5) 0.1022(3) 0.0927(3) 0.0168(7) Uani 1 1 d . . . C6 C 0.7952(5) 0.2193(3) 0.1212(3) 0.0187(8) Uani 1 1 d . . . H6 H 0.8299 0.2284 0.1910 0.022 Uiso 1 1 calc R . . C7 C 0.6768(7) 0.3819(4) 0.0479(4) 0.0319(11) Uani 1 1 d . . . H7A H 0.6331 0.4337 0.0798 0.038 Uiso 1 1 calc R . . H7B H 0.6255 0.3965 -0.0212 0.038 Uiso 1 1 calc R . . C8 C 0.8699(6) 0.3891(3) 0.0880(3) 0.0232(9) Uani 1 1 d . . . H8A H 0.9056 0.4320 0.0462 0.028 Uiso 1 1 calc R . . H8B H 0.9182 0.4197 0.1527 0.028 Uiso 1 1 calc R . . C9 C 1.0997(5) 0.2540(4) 0.1513(3) 0.0195(8) Uani 1 1 d . . . C10 C 1.1524(6) 0.1718(4) 0.2190(4) 0.0319(11) Uani 1 1 d . . . H10 H 1.0728 0.1290 0.2292 0.038 Uiso 1 1 calc R . . C11 C 1.3270(7) 0.1536(5) 0.2719(5) 0.0460(16) Uani 1 1 d . . . H11 H 1.3632 0.0976 0.3169 0.055 Uiso 1 1 calc R . . C12 C 1.4454(7) 0.2169(6) 0.2584(4) 0.0450(16) Uani 1 1 d . . . H12 H 1.5611 0.2035 0.2936 0.054 Uiso 1 1 calc R . . C13 C 1.3927(7) 0.3000(7) 0.1929(4) 0.0481(17) Uani 1 1 d . . . H13 H 1.4733 0.3435 0.1844 0.058 Uiso 1 1 calc R . . C14 C 1.2198(7) 0.3202(5) 0.1390(4) 0.0372(13) Uani 1 1 d . . . H14 H 1.1849 0.3773 0.0952 0.045 Uiso 1 1 calc R . . Cl1 Cl 0.94210(17) 0.35446(9) -0.10710(8) 0.0299(3) Uani 1 1 d . . . Cl2 Cl 0.82920(14) 0.10920(9) -0.18401(7) 0.0230(2) Uani 1 1 d . . . N1 N 0.7935(4) 0.0765(3) 0.0124(2) 0.0157(6) Uani 1 1 d . . . N2 N 0.9195(4) 0.2726(3) 0.0890(2) 0.0159(6) Uani 1 1 d . . . O1 O 0.6401(4) 0.2735(3) 0.0669(3) 0.0286(7) Uani 1 1 d . . . Pd1 Pd 0.87166(4) 0.20202(2) -0.04530(2) 0.01447(9) 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 0.021(2) 0.0176(19) 0.0186(18) -0.0022(15) 0.0067(16) -0.0007(16) C2 0.030(2) 0.0138(19) 0.030(2) -0.0027(17) 0.0127(19) -0.0044(17) C3 0.033(2) 0.022(2) 0.028(2) 0.0041(17) 0.0138(19) -0.0067(19) C4 0.030(2) 0.026(2) 0.022(2) -0.0015(17) 0.0146(18) -0.0083(19) C5 0.0161(17) 0.0186(19) 0.0150(17) 0.0003(14) 0.0059(14) -0.0017(15) C6 0.0181(18) 0.020(2) 0.0197(18) -0.0006(15) 0.0093(15) 0.0019(15) C7 0.034(3) 0.024(2) 0.032(2) -0.0012(19) 0.009(2) 0.010(2) C8 0.034(2) 0.0128(18) 0.024(2) -0.0038(16) 0.0143(18) -0.0025(17) C9 0.0187(19) 0.022(2) 0.0170(18) -0.0086(15) 0.0070(15) -0.0015(16) C10 0.023(2) 0.021(2) 0.037(3) -0.0001(19) -0.0016(19) -0.0028(18) C11 0.031(3) 0.026(3) 0.054(3) -0.007(2) -0.009(3) 0.005(2) C12 0.018(2) 0.062(4) 0.045(3) -0.030(3) 0.002(2) 0.002(2) C13 0.025(2) 0.092(5) 0.031(3) -0.017(3) 0.015(2) -0.021(3) C14 0.027(2) 0.063(4) 0.021(2) -0.001(2) 0.0102(19) -0.014(2) Cl1 0.0477(7) 0.0226(5) 0.0208(5) 0.0007(4) 0.0157(5) -0.0125(5) Cl2 0.0321(5) 0.0221(5) 0.0157(4) -0.0022(4) 0.0109(4) -0.0004(4) N1 0.0153(15) 0.0161(16) 0.0140(14) -0.0017(12) 0.0044(12) -0.0015(12) N2 0.0184(16) 0.0137(15) 0.0161(15) 0.0002(12) 0.0077(13) -0.0015(12) O1 0.0198(15) 0.0240(17) 0.0401(19) -0.0048(14) 0.0107(14) 0.0037(13) Pd1 0.01723(14) 0.01385(14) 0.01247(13) -0.00003(11) 0.00635(10) -0.00142(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 C1 N1 1.351(5) . ? C1 C2 1.378(6) . ? C1 H1 0.9300 . ? C2 C3 1.388(7) . ? C2 H2 0.9300 . ? C3 C4 1.391(6) . ? C3 H3 0.9300 . ? C4 C5 1.373(6) . ? C4 H4 0.9300 . ? C5 N1 1.356(5) . ? C5 C6 1.501(6) . ? C6 O1 1.414(5) . ? C6 N2 1.505(5) . ? C6 H6 0.9800 . ? C7 O1 1.435(6) . ? C7 C8 1.519(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N2 1.501(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.381(7) . ? C9 C14 1.393(7) . ? C9 N2 1.462(5) . ? C10 C11 1.399(7) . ? C10 H10 0.9300 . ? C11 C12 1.368(10) . ? C11 H11 0.9300 . ? C12 C13 1.370(10) . ? C12 H12 0.9300 . ? C13 C14 1.392(8) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? Cl1 Pd1 2.2982(11) . ? Cl2 Pd1 2.2899(10) . ? N1 Pd1 2.031(3) . ? N2 Pd1 2.095(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 N1 C1 C2 121.8(4) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C1 C2 C3 119.6(4) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 118.7(4) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 119.0(4) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N1 C5 C4 122.4(4) . . ? N1 C5 C6 115.2(3) . . ? C4 C5 C6 122.4(4) . . ? O1 C6 C5 107.4(3) . . ? O1 C6 N2 103.4(3) . . ? C5 C6 N2 111.6(3) . . ? O1 C6 H6 111.3 . . ? C5 C6 H6 111.3 . . ? N2 C6 H6 111.3 . . ? O1 C7 C8 105.7(4) . . ? O1 C7 H7A 110.6 . . ? C8 C7 H7A 110.6 . . ? O1 C7 H7B 110.6 . . ? C8 C7 H7B 110.6 . . ? H7A C7 H7B 108.7 . . ? N2 C8 C7 102.0(3) . . ? N2 C8 H8A 111.4 . . ? C7 C8 H8A 111.4 . . ? N2 C8 H8B 111.4 . . ? C7 C8 H8B 111.4 . . ? H8A C8 H8B 109.2 . . ? C10 C9 C14 120.0(4) . . ? C10 C9 N2 121.8(4) . . ? C14 C9 N2 118.1(4) . . ? C9 C10 C11 119.1(5) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C12 C11 C10 121.0(6) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 119.7(5) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C12 C13 C14 120.8(6) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C13 C14 C9 119.4(6) . . ? C13 C14 H14 120.3 . . ? C9 C14 H14 120.3 . . ? C1 N1 C5 118.5(4) . . ? C1 N1 Pd1 127.2(3) . . ? C5 N1 Pd1 114.3(3) . . ? C9 N2 C8 112.3(3) . . ? C9 N2 C6 115.5(3) . . ? C8 N2 C6 100.7(3) . . ? C9 N2 Pd1 106.7(2) . . ? C8 N2 Pd1 116.8(3) . . ? C6 N2 Pd1 104.8(2) . . ? C6 O1 C7 109.0(3) . . ? N1 Pd1 N2 82.23(13) . . ? N1 Pd1 Cl2 93.40(10) . . ? N2 Pd1 Cl2 174.35(10) . . ? N1 Pd1 Cl1 174.39(10) . . ? N2 Pd1 Cl1 94.41(10) . . ? Cl2 Pd1 Cl1 90.22(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 N1 C1 C2 C3 -2.1(7) . . . . ? C1 C2 C3 C4 1.2(7) . . . . ? C2 C3 C4 C5 0.5(7) . . . . ? C3 C4 C5 N1 -1.4(7) . . . . ? C3 C4 C5 C6 175.6(4) . . . . ? N1 C5 C6 O1 84.8(4) . . . . ? C4 C5 C6 O1 -92.5(5) . . . . ? N1 C5 C6 N2 -28.0(5) . . . . ? C4 C5 C6 N2 154.8(4) . . . . ? O1 C7 C8 N2 22.5(4) . . . . ? C14 C9 C10 C11 -2.4(8) . . . . ? N2 C9 C10 C11 175.8(5) . . . . ? C9 C10 C11 C12 0.9(9) . . . . ? C10 C11 C12 C13 0.7(9) . . . . ? C11 C12 C13 C14 -0.8(9) . . . . ? C12 C13 C14 C9 -0.7(9) . . . . ? C10 C9 C14 C13 2.3(8) . . . . ? N2 C9 C14 C13 -176.0(5) . . . . ? C2 C1 N1 C5 1.3(6) . . . . ? C2 C1 N1 Pd1 -178.8(3) . . . . ? C4 C5 N1 C1 0.5(6) . . . . ? C6 C5 N1 C1 -176.7(4) . . . . ? C4 C5 N1 Pd1 -179.4(3) . . . . ? C6 C5 N1 Pd1 3.3(4) . . . . ? C10 C9 N2 C8 131.2(4) . . . . ? C14 C9 N2 C8 -50.5(5) . . . . ? C10 C9 N2 C6 16.5(6) . . . . ? C14 C9 N2 C6 -165.2(4) . . . . ? C10 C9 N2 Pd1 -99.5(4) . . . . ? C14 C9 N2 Pd1 78.7(4) . . . . ? C7 C8 N2 C9 -162.6(4) . . . . ? C7 C8 N2 C6 -39.1(4) . . . . ? C7 C8 N2 Pd1 73.6(4) . . . . ? O1 C6 N2 C9 164.1(3) . . . . ? C5 C6 N2 C9 -80.7(4) . . . . ? O1 C6 N2 C8 42.9(4) . . . . ? C5 C6 N2 C8 158.1(3) . . . . ? O1 C6 N2 Pd1 -78.7(3) . . . . ? C5 C6 N2 Pd1 36.5(4) . . . . ? C5 C6 O1 C7 -147.9(4) . . . . ? N2 C6 O1 C7 -29.8(4) . . . . ? C8 C7 O1 C6 4.5(5) . . . . ? C1 N1 Pd1 N2 -165.5(4) . . . . ? C5 N1 Pd1 N2 14.4(3) . . . . ? C1 N1 Pd1 Cl2 10.9(3) . . . . ? C5 N1 Pd1 Cl2 -169.2(3) . . . . ? C1 N1 Pd1 Cl1 141.1(8) . . . . ? C5 N1 Pd1 Cl1 -39.0(11) . . . . ? C9 N2 Pd1 N1 95.7(3) . . . . ? C8 N2 Pd1 N1 -137.7(3) . . . . ? C6 N2 Pd1 N1 -27.3(2) . . . . ? C9 N2 Pd1 Cl2 56.3(11) . . . . ? C8 N2 Pd1 Cl2 -177.1(9) . . . . ? C6 N2 Pd1 Cl2 -66.8(11) . . . . ? C9 N2 Pd1 Cl1 -88.8(3) . . . . ? C8 N2 Pd1 Cl1 37.8(3) . . . . ? C6 N2 Pd1 Cl1 148.2(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.18 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.856 _refine_diff_density_min -1.168 _refine_diff_density_rms 0.130 #===END data_d:complex2 _database_code_depnum_ccdc_archive 'CCDC 830384' #TrackingRef 'structures_dalton2011.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 Cl2 N4 Ni O2' _chemical_formula_sum 'C28 H28 Cl2 N4 Ni O2' _chemical_formula_weight 582.15 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' Ni Ni 0.3393 1.1124 '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' _symmetry_Int_Tables_number 15 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 23.437(5) _cell_length_b 6.6280(10) _cell_length_c 17.741(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.67(3) _cell_angle_gamma 90.00 _cell_volume 2724.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4357 _cell_measurement_theta_min 1.25 _cell_measurement_theta_max 28.20 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.941 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.580 _exptl_absorpt_correction_T_max 0.873 _exptl_absorpt_process_details 'Walker, N. & Stuart, D. (1983)' _exptl_special_details ; A crystal was mounted at 173K on a Stoe Image Plate Diffraction System (Stoe & Cie, 2000) using MoK\a graphite monochromated radiation. Image plate distance 70mm, \f oscillation scans 0 - 200\%, step \D\f = 1.0\%, 3 minutes per frame. ; _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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12433 _diffrn_reflns_av_R_equivalents 0.2128 _diffrn_reflns_av_sigmaI/netI 0.2091 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 29.19 _reflns_number_total 3659 _reflns_number_gt 1812 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe & Cie, 2000)' _computing_cell_refinement 'CELL (Stoe & Cie, 2000)' _computing_data_reduction 'INTEGRATE (Stoe & Cie, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-32 (Farrugia, 1997)' _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^)+(0.0255P)^2^] 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 3659 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1891 _refine_ls_R_factor_gt 0.0890 _refine_ls_wR_factor_ref 0.1412 _refine_ls_wR_factor_gt 0.1166 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _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 C1 C 0.2399(2) 0.9822(8) 0.3508(3) 0.0257(12) Uani 1 1 d . . . H1 H 0.2769 1.0286 0.3689 0.031 Uiso 1 1 calc R . . C2 C 0.2154(3) 1.0327(9) 0.2765(3) 0.0317(14) Uani 1 1 d . . . H2 H 0.2356 1.1094 0.2454 0.038 Uiso 1 1 calc R . . C3 C 0.1600(3) 0.9646(9) 0.2508(3) 0.0319(14) Uani 1 1 d . . . H3 H 0.1420 0.9982 0.2020 0.038 Uiso 1 1 calc R . . C4 C 0.1312(3) 0.8463(8) 0.2976(3) 0.0289(13) Uani 1 1 d . . . H4 H 0.0945 0.7967 0.2803 0.035 Uiso 1 1 calc R . . C5 C 0.1588(2) 0.8036(7) 0.3713(3) 0.0214(12) Uani 1 1 d . . . C6 C 0.1312(2) 0.6786(7) 0.4291(3) 0.0210(11) Uani 1 1 d . . . H6 H 0.1142 0.7690 0.4634 0.025 Uiso 1 1 calc R . . C7 C 0.1754(2) 0.3714(8) 0.4267(3) 0.0286(14) Uani 1 1 d . . . H7A H 0.1932 0.2600 0.4570 0.034 Uiso 1 1 calc R . . H7B H 0.1955 0.3924 0.3834 0.034 Uiso 1 1 calc R . . C8 C 0.1114(2) 0.3330(8) 0.4011(4) 0.0327(14) Uani 1 1 d . . . H8A H 0.1048 0.2617 0.3528 0.039 Uiso 1 1 calc R . . H8B H 0.0947 0.2561 0.4389 0.039 Uiso 1 1 calc R . . C9 C 0.0296(2) 0.5736(8) 0.3958(3) 0.0262(12) Uani 1 1 d . . . C10 C 0.0096(2) 0.7701(10) 0.4058(3) 0.0294(13) Uani 1 1 d . . . H10 H 0.0354 0.8777 0.4103 0.035 Uiso 1 1 calc R . . C11 C -0.0484(2) 0.8048(9) 0.4090(3) 0.0329(15) Uani 1 1 d . . . H11 H -0.0610 0.9354 0.4164 0.039 Uiso 1 1 calc R . . C12 C -0.0877(3) 0.6480(10) 0.4014(4) 0.0407(16) Uani 1 1 d . . . H12 H -0.1265 0.6720 0.4041 0.049 Uiso 1 1 calc R . . C13 C -0.0687(3) 0.4559(10) 0.3898(4) 0.0404(16) Uani 1 1 d . . . H13 H -0.0948 0.3496 0.3840 0.049 Uiso 1 1 calc R . . C14 C -0.0109(2) 0.4190(9) 0.3867(3) 0.0333(14) Uani 1 1 d . . . H14 H 0.0011 0.2881 0.3783 0.040 Uiso 1 1 calc R . . N1 N 0.21240(18) 0.8689(6) 0.3975(2) 0.0203(10) Uani 1 1 d . . . N2 N 0.08759(19) 0.5380(7) 0.3935(3) 0.0252(10) Uani 1 1 d . . . O1 O 0.17535(15) 0.5559(5) 0.4728(2) 0.0222(8) Uani 1 1 d . . . Cl1 Cl 0.19164(6) 0.9578(2) 0.56740(8) 0.0272(3) Uani 1 1 d . . . Ni1 Ni 0.2500 0.7500 0.5000 0.0189(2) Uani 1 2 d S . . 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 0.032(3) 0.019(3) 0.027(3) -0.002(2) 0.010(2) -0.006(3) C2 0.041(4) 0.030(3) 0.026(3) 0.004(3) 0.011(3) -0.007(3) C3 0.035(3) 0.036(3) 0.023(3) 0.009(3) -0.001(2) 0.000(3) C4 0.029(3) 0.029(3) 0.026(3) -0.003(2) -0.002(2) -0.005(3) C5 0.026(3) 0.017(3) 0.024(3) -0.001(2) 0.011(2) 0.001(2) C6 0.015(2) 0.018(2) 0.029(3) 0.001(2) 0.000(2) 0.002(2) C7 0.035(3) 0.012(3) 0.039(4) -0.002(2) 0.005(3) 0.002(3) C8 0.032(3) 0.022(3) 0.045(4) -0.004(3) 0.006(3) 0.003(3) C9 0.025(3) 0.025(3) 0.027(3) 0.001(2) 0.001(2) -0.005(3) C10 0.023(3) 0.032(3) 0.033(3) 0.000(3) 0.001(2) -0.009(3) C11 0.023(3) 0.031(4) 0.043(4) 0.003(2) 0.001(3) 0.001(3) C12 0.025(3) 0.046(4) 0.051(4) 0.008(3) 0.007(3) 0.000(3) C13 0.023(3) 0.039(4) 0.058(4) 0.007(3) 0.000(3) -0.012(3) C14 0.028(3) 0.025(3) 0.045(4) 0.002(3) 0.003(3) -0.008(3) N1 0.022(2) 0.022(2) 0.019(2) 0.0010(18) 0.0063(18) -0.003(2) N2 0.022(2) 0.019(2) 0.034(3) -0.001(2) 0.002(2) -0.006(2) O1 0.022(2) 0.0185(18) 0.026(2) 0.0021(16) 0.0036(15) 0.0063(17) Cl1 0.0268(7) 0.0284(7) 0.0274(7) -0.0041(6) 0.0068(6) 0.0046(7) Ni1 0.0201(5) 0.0184(5) 0.0182(5) -0.0003(5) 0.0029(4) 0.0021(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 N1 1.352(6) . ? C1 C2 1.396(7) . ? C1 H1 0.9300 . ? C2 C3 1.386(8) . ? C2 H2 0.9300 . ? C3 C4 1.388(8) . ? C3 H3 0.9300 . ? C4 C5 1.398(7) . ? C4 H4 0.9300 . ? C5 N1 1.344(6) . ? C5 C6 1.534(7) . ? C6 O1 1.446(6) . ? C6 N2 1.456(6) . ? C6 H6 0.9800 . ? C7 O1 1.471(6) . ? C7 C8 1.522(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N2 1.467(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.386(7) . ? C9 C14 1.389(7) . ? C9 C10 1.405(8) . ? C10 C11 1.389(7) . ? C10 H10 0.9300 . ? C11 C12 1.382(8) . ? C11 H11 0.9300 . ? C12 C13 1.375(9) . ? C12 H12 0.9300 . ? C13 C14 1.386(8) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? N1 Ni1 2.055(4) . ? O1 Ni1 2.167(3) . ? Cl1 Ni1 2.3857(14) . ? Ni1 N1 2.055(4) 7_566 ? Ni1 O1 2.167(4) 7_566 ? Ni1 Cl1 2.3857(14) 7_566 ? 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 C1 C2 123.1(5) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 117.7(5) . . ? C3 C2 H2 121.2 . . ? C1 C2 H2 121.2 . . ? C2 C3 C4 120.1(5) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 118.5(5) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? N1 C5 C4 122.3(5) . . ? N1 C5 C6 114.1(4) . . ? C4 C5 C6 123.6(5) . . ? O1 C6 N2 105.8(4) . . ? O1 C6 C5 108.8(4) . . ? N2 C6 C5 113.3(4) . . ? O1 C6 H6 109.6 . . ? N2 C6 H6 109.6 . . ? C5 C6 H6 109.6 . . ? O1 C7 C8 102.9(4) . . ? O1 C7 H7A 111.2 . . ? C8 C7 H7A 111.2 . . ? O1 C7 H7B 111.2 . . ? C8 C7 H7B 111.2 . . ? H7A C7 H7B 109.1 . . ? N2 C8 C7 102.5(4) . . ? N2 C8 H8A 111.3 . . ? C7 C8 H8A 111.3 . . ? N2 C8 H8B 111.3 . . ? C7 C8 H8B 111.3 . . ? H8A C8 H8B 109.2 . . ? N2 C9 C14 121.8(5) . . ? N2 C9 C10 120.6(5) . . ? C14 C9 C10 117.6(5) . . ? C11 C10 C9 120.4(5) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 120.9(6) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C13 C12 C11 119.0(6) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 120.7(6) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C13 C14 C9 121.3(6) . . ? C13 C14 H14 119.4 . . ? C9 C14 H14 119.4 . . ? C5 N1 C1 118.3(5) . . ? C5 N1 Ni1 115.9(3) . . ? C1 N1 Ni1 125.1(4) . . ? C9 N2 C6 120.4(4) . . ? C9 N2 C8 121.0(4) . . ? C6 N2 C8 108.7(4) . . ? C6 O1 C7 103.3(4) . . ? C6 O1 Ni1 105.9(3) . . ? C7 O1 Ni1 123.4(3) . . ? N1 Ni1 N1 180.000(1) 7_566 . ? N1 Ni1 O1 78.82(15) 7_566 7_566 ? N1 Ni1 O1 101.18(15) . 7_566 ? N1 Ni1 O1 101.18(15) 7_566 . ? N1 Ni1 O1 78.82(15) . . ? O1 Ni1 O1 180.00(12) 7_566 . ? N1 Ni1 Cl1 88.83(12) 7_566 . ? N1 Ni1 Cl1 91.17(12) . . ? O1 Ni1 Cl1 92.87(10) 7_566 . ? O1 Ni1 Cl1 87.13(10) . . ? N1 Ni1 Cl1 91.17(12) 7_566 7_566 ? N1 Ni1 Cl1 88.83(12) . 7_566 ? O1 Ni1 Cl1 87.13(10) 7_566 7_566 ? O1 Ni1 Cl1 92.87(10) . 7_566 ? Cl1 Ni1 Cl1 180.00(5) . 7_566 ? 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 N1 C1 C2 C3 0.9(8) . . . . ? C1 C2 C3 C4 -1.5(9) . . . . ? C2 C3 C4 C5 1.9(9) . . . . ? C3 C4 C5 N1 -1.6(8) . . . . ? C3 C4 C5 C6 178.7(5) . . . . ? N1 C5 C6 O1 -36.7(6) . . . . ? C4 C5 C6 O1 143.0(5) . . . . ? N1 C5 C6 N2 -154.1(4) . . . . ? C4 C5 C6 N2 25.6(7) . . . . ? O1 C7 C8 N2 32.9(5) . . . . ? N2 C9 C10 C11 -179.2(5) . . . . ? C14 C9 C10 C11 2.3(8) . . . . ? C9 C10 C11 C12 -1.0(9) . . . . ? C10 C11 C12 C13 -0.6(9) . . . . ? C11 C12 C13 C14 0.8(10) . . . . ? C12 C13 C14 C9 0.6(10) . . . . ? N2 C9 C14 C13 179.4(6) . . . . ? C10 C9 C14 C13 -2.1(8) . . . . ? C4 C5 N1 C1 1.0(7) . . . . ? C6 C5 N1 C1 -179.3(4) . . . . ? C4 C5 N1 Ni1 -170.0(4) . . . . ? C6 C5 N1 Ni1 9.8(5) . . . . ? C2 C1 N1 C5 -0.6(8) . . . . ? C2 C1 N1 Ni1 169.4(4) . . . . ? C14 C9 N2 C6 -157.9(5) . . . . ? C10 C9 N2 C6 23.7(8) . . . . ? C14 C9 N2 C8 -15.9(8) . . . . ? C10 C9 N2 C8 165.6(5) . . . . ? O1 C6 N2 C9 133.1(5) . . . . ? C5 C6 N2 C9 -107.7(5) . . . . ? O1 C6 N2 C8 -13.0(6) . . . . ? C5 C6 N2 C8 106.2(5) . . . . ? C7 C8 N2 C9 -158.4(5) . . . . ? C7 C8 N2 C6 -12.5(6) . . . . ? N2 C6 O1 C7 34.0(5) . . . . ? C5 C6 O1 C7 -88.0(5) . . . . ? N2 C6 O1 Ni1 164.9(3) . . . . ? C5 C6 O1 Ni1 42.9(4) . . . . ? C8 C7 O1 C6 -41.5(5) . . . . ? C8 C7 O1 Ni1 -161.0(3) . . . . ? C5 N1 Ni1 N1 -152(100) . . . 7_566 ? C1 N1 Ni1 N1 38(100) . . . 7_566 ? C5 N1 Ni1 O1 -168.6(3) . . . 7_566 ? C1 N1 Ni1 O1 21.2(4) . . . 7_566 ? C5 N1 Ni1 O1 11.4(3) . . . . ? C1 N1 Ni1 O1 -158.8(4) . . . . ? C5 N1 Ni1 Cl1 -75.4(3) . . . . ? C1 N1 Ni1 Cl1 114.4(4) . . . . ? C5 N1 Ni1 Cl1 104.6(3) . . . 7_566 ? C1 N1 Ni1 Cl1 -65.6(4) . . . 7_566 ? C6 O1 Ni1 N1 149.6(3) . . . 7_566 ? C7 O1 Ni1 N1 -92.1(4) . . . 7_566 ? C6 O1 Ni1 N1 -30.4(3) . . . . ? C7 O1 Ni1 N1 87.9(4) . . . . ? C6 O1 Ni1 O1 6(100) . . . 7_566 ? C7 O1 Ni1 O1 124(100) . . . 7_566 ? C6 O1 Ni1 Cl1 61.4(3) . . . . ? C7 O1 Ni1 Cl1 179.6(3) . . . . ? C6 O1 Ni1 Cl1 -118.6(3) . . . 7_566 ? C7 O1 Ni1 Cl1 -0.4(3) . . . 7_566 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 29.19 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.453 _refine_diff_density_min -0.616 _refine_diff_density_rms 0.107