# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_tdka1-041a-def _database_code_depnum_ccdc_archive 'CCDC 915130' #TrackingRef 'NiAS-DEF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena{[2,2'-dihydroxy-4,4'-dicarboxylato-bis(diethylformamido)- nickel(II)] DEF-solvate} ; _chemical_name_common ; catena((2,2'-dihydroxy-4,4'-dicarboxylato- bis(diethylformamido)-nickel(ii)) DEF-solvate) ; _chemical_melting_point N/A _chemical_formula_moiety 'C24 H28 N2 Ni O8' _chemical_formula_sum 'C24 H28 N2 Ni O8' _chemical_formula_weight 531.19 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' Ni Ni 0.3393 1.1124 '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' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 31 2 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' 'y, x, -z' '-x+y, -x, z+2/3' '-x, -x+y, -z+1/3' 'x-y, -y, -z+2/3' _cell_length_a 17.3278(4) _cell_length_b 17.3278(4) _cell_length_c 9.1188(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2371.13(11) _cell_formula_units_Z 3 _cell_measurement_temperature 150.0 _cell_measurement_reflns_used 5829 _cell_measurement_theta_min 2.6084 _cell_measurement_theta_max 29.2469 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.116 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 834 _exptl_absorpt_coefficient_mu 0.653 _exptl_absorpt_correction_T_min 0.82567 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1695 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16981 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_unetI/netI 0.0428 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 26.99 _reflns_number_total 3456 _reflns_number_gt 3354 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond 3.2g (Crystal Impact, 2012)' _computing_publication_material 'SHELXS-97 (Sheldrick, 2008)' _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^ > 2\s(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. Hydrogen atoms on the phenyl rings and DEF were fixed in position in geometrically calculated positions and refined in riding mode on the parent atom. C-C and C-N distances on the ethyl groups of the disordered DEF molecules were restrained to literature values. ; _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^)+(0.0951P)^2^+15.6654P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(1) _refine_ls_number_reflns 3456 _refine_ls_number_parameters 154 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0948 _refine_ls_R_factor_gt 0.0931 _refine_ls_wR_factor_ref 0.2592 _refine_ls_wR_factor_gt 0.2582 _refine_ls_goodness_of_fit_ref 1.228 _refine_ls_restrained_S_all 1.227 _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 C4 C 0.2860(5) 0.4773(4) 0.4347(8) 0.0162(14) Uani 1 1 d . . . H4 H 0.3075 0.5378 0.4485 0.019 Uiso 1 1 calc R . . C2 C 0.2085(5) 0.4287(4) 0.3565(9) 0.0186(15) Uani 1 1 d . . . C5 C 0.2261(5) 0.2997(5) 0.3879(9) 0.0210(15) Uani 1 1 d . . . H5 H 0.2061 0.2398 0.3700 0.025 Uiso 1 1 calc R . . C3 C 0.1774(5) 0.3374(4) 0.3305(8) 0.0183(15) Uani 1 1 d . . . H3 H 0.1257 0.3030 0.2766 0.022 Uiso 1 1 calc R . . C6 C 0.3333(4) 0.4400(5) 0.4937(8) 0.0168(13) Uani 1 1 d . . . C7 C 0.3027(4) 0.3482(4) 0.4700(8) 0.0136(13) Uani 1 1 d . . . O3 O 0.4067(3) 0.4883(3) 0.5779(6) 0.0186(11) Uani 1 1 d . . . O21 O 0.0677(4) 0.4966(6) -0.0281(6) 0.0394(16) Uani 1 1 d . . . N21A N 0.0914(8) 0.5686(9) -0.2558(14) 0.024(3) Uiso 0.452(12) 1 d PD A 1 C21A C 0.0524(10) 0.5442(9) -0.1282(15) 0.014(3) Uiso 0.452(12) 1 d P A 1 H21A H 0.0107 0.5611 -0.1049 0.017 Uiso 0.452(12) 1 calc PR A 1 C23A C 0.0686(13) 0.6106(10) -0.3722(19) 0.039(4) Uiso 0.452(12) 1 d PD A 1 H23A H 0.0128 0.6068 -0.3443 0.047 Uiso 0.452(12) 1 calc PR A 1 H23B H 0.0562 0.5735 -0.4586 0.047 Uiso 0.452(12) 1 calc PR A 1 C25A C 0.1715(8) 0.5661(10) -0.2935(16) 0.017(3) Uiso 0.452(12) 1 d PD A 1 H25A H 0.1798 0.5722 -0.3989 0.021 Uiso 0.452(12) 1 calc PR A 1 H25B H 0.1636 0.5086 -0.2659 0.021 Uiso 0.452(12) 1 calc PR A 1 C24A C 0.1309(16) 0.7067(11) -0.421(3) 0.048(6) Uiso 0.452(12) 1 d PD A 1 H24A H 0.1031 0.7220 -0.4979 0.072 Uiso 0.452(12) 1 calc PR A 1 H24B H 0.1857 0.7124 -0.4565 0.072 Uiso 0.452(12) 1 calc PR A 1 H24C H 0.1431 0.7461 -0.3393 0.072 Uiso 0.452(12) 1 calc PR A 1 C26A C 0.2554(13) 0.6393(16) -0.219(3) 0.057(7) Uiso 0.452(12) 1 d PD A 1 H26A H 0.3059 0.6340 -0.2476 0.086 Uiso 0.452(12) 1 calc PR A 1 H26B H 0.2483 0.6331 -0.1143 0.086 Uiso 0.452(12) 1 calc PR A 1 H26C H 0.2648 0.6966 -0.2477 0.086 Uiso 0.452(12) 1 calc PR A 1 N21B N 0.1408(12) 0.4453(11) -0.1679(19) 0.052(5) Uiso 0.548(12) 1 d PD A 2 C21B C 0.0861(11) 0.4348(11) -0.0698(17) 0.031(4) Uiso 0.548(12) 1 d P A 2 H21B H 0.0565 0.3798 -0.0231 0.037 Uiso 0.548(12) 1 calc PR A 2 C23B C 0.1526(16) 0.3713(12) -0.211(3) 0.059(6) Uiso 0.548(12) 1 d PD A 2 H23C H 0.1946 0.3685 -0.1434 0.070 Uiso 0.548(12) 1 calc PR A 2 H23D H 0.1791 0.3832 -0.3076 0.070 Uiso 0.548(12) 1 calc PR A 2 C25B C 0.1384(19) 0.5048(17) -0.277(3) 0.097(10) Uiso 0.548(12) 1 d PD A 2 H25C H 0.0879 0.5138 -0.2642 0.116 Uiso 0.548(12) 1 calc PR A 2 H25D H 0.1384 0.4845 -0.3765 0.116 Uiso 0.548(12) 1 calc PR A 2 C24B C 0.068(2) 0.280(2) -0.213(6) 0.16(2) Uiso 0.548(12) 1 d PD A 2 H24D H 0.0814 0.2357 -0.2452 0.237 Uiso 0.548(12) 1 calc PR A 2 H24E H 0.0252 0.2818 -0.2787 0.237 Uiso 0.548(12) 1 calc PR A 2 H24F H 0.0426 0.2656 -0.1159 0.237 Uiso 0.548(12) 1 calc PR A 2 C26B C 0.227(2) 0.588(2) -0.238(4) 0.100(11) Uiso 0.548(12) 1 d PD A 2 H26D H 0.2373 0.6355 -0.3037 0.149 Uiso 0.548(12) 1 calc PR A 2 H26E H 0.2743 0.5749 -0.2466 0.149 Uiso 0.548(12) 1 calc PR A 2 H26F H 0.2240 0.6053 -0.1392 0.149 Uiso 0.548(12) 1 calc PR A 2 Ni1 Ni 0.0000 0.46492(6) 0.1667 0.0143(3) Uani 1 2 d S . . O1 O 0.0839(3) 0.4242(3) 0.2412(7) 0.0264(13) Uani 1 1 d . . . O2 O 0.1934(4) 0.5560(4) 0.3216(8) 0.0396(17) Uani 1 1 d . . . C1 C 0.1567(4) 0.4715(5) 0.3019(8) 0.0158(14) Uani 1 1 d . A . 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 C4 0.010(3) 0.004(3) 0.033(4) -0.004(3) -0.006(3) 0.002(2) C2 0.016(3) 0.005(3) 0.035(4) -0.001(3) -0.003(3) 0.006(3) C5 0.015(3) 0.013(3) 0.035(4) 0.003(3) 0.000(3) 0.007(3) C3 0.018(3) 0.009(3) 0.027(3) -0.008(2) -0.008(3) 0.006(2) C6 0.008(3) 0.010(3) 0.028(3) -0.003(3) 0.001(2) 0.002(3) C7 0.013(3) 0.012(3) 0.021(3) -0.002(3) -0.003(3) 0.010(3) O3 0.012(2) 0.012(2) 0.035(3) -0.0020(19) -0.005(2) 0.0087(18) O21 0.028(3) 0.077(5) 0.021(3) -0.009(3) 0.005(2) 0.032(3) Ni1 0.0175(6) 0.0110(4) 0.0166(5) -0.0026(3) -0.0052(5) 0.0088(3) O1 0.019(3) 0.016(3) 0.042(3) -0.005(2) -0.020(2) 0.007(2) O2 0.025(3) 0.015(3) 0.082(5) -0.003(3) -0.024(3) 0.013(2) C1 0.011(3) 0.013(3) 0.021(3) -0.002(3) -0.002(3) 0.005(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C4 C2 1.375(10) . ? C4 C6 1.380(10) . ? C4 H4 0.9300 . ? C2 C3 1.413(9) . ? C2 C1 1.507(10) . ? C5 C7 1.384(10) . ? C5 C3 1.401(10) . ? C5 H5 0.9300 . ? C3 H3 0.9300 . ? C6 O3 1.358(8) . ? C6 C7 1.420(9) . ? C7 C7 1.470(12) 3_556 ? O3 Ni1 2.076(5) 2_665 ? O21 C21B 1.318(18) . ? O21 C21A 1.342(16) . ? O21 Ni1 2.046(6) . ? N21A C21A 1.306(18) . ? N21A C23A 1.4498(10) . ? N21A C25A 1.4499(10) . ? C21A H21A 0.9300 . ? C23A C24A 1.5300(10) . ? C23A H23A 0.9700 . ? C23A H23B 0.9700 . ? C25A C26A 1.5300(10) . ? C25A H25A 0.9700 . ? C25A H25B 0.9700 . ? C24A H24A 0.9600 . ? C24A H24B 0.9600 . ? C24A H24C 0.9600 . ? C26A H26A 0.9600 . ? C26A H26B 0.9600 . ? C26A H26C 0.9600 . ? N21B C21B 1.25(2) . ? N21B C25B 1.4501(10) . ? N21B C23B 1.4501(10) . ? C21B H21B 0.9300 . ? C23B C24B 1.5301(10) . ? C23B H23C 0.9700 . ? C23B H23D 0.9700 . ? C25B C26B 1.5299(10) . ? C25B H25C 0.9700 . ? C25B H25D 0.9700 . ? C24B H24D 0.9600 . ? C24B H24E 0.9600 . ? C24B H24F 0.9600 . ? C26B H26D 0.9600 . ? C26B H26E 0.9600 . ? C26B H26F 0.9600 . ? Ni1 O1 2.025(5) . ? Ni1 O1 2.025(5) 5 ? Ni1 O21 2.046(6) 5 ? Ni1 O3 2.076(5) 4_564 ? Ni1 O3 2.076(5) 6_565 ? O1 C1 1.239(8) . ? O2 C1 1.285(9) . ? 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 C2 C4 C6 122.8(6) . . ? C2 C4 H4 118.6 . . ? C6 C4 H4 118.6 . . ? C4 C2 C3 118.8(6) . . ? C4 C2 C1 120.6(6) . . ? C3 C2 C1 120.5(6) . . ? C7 C5 C3 122.5(7) . . ? C7 C5 H5 118.7 . . ? C3 C5 H5 118.7 . . ? C5 C3 C2 118.5(7) . . ? C5 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? O3 C6 C4 121.6(6) . . ? O3 C6 C7 119.1(6) . . ? C4 C6 C7 119.3(6) . . ? C5 C7 C6 118.0(6) . . ? C5 C7 C7 119.0(5) . 3_556 ? C6 C7 C7 123.0(5) . 3_556 ? C6 O3 Ni1 122.5(4) . 2_665 ? C21B O21 C21A 120.3(10) . . ? C21B O21 Ni1 111.8(9) . . ? C21A O21 Ni1 119.5(7) . . ? C21A N21A C23A 126.0(13) . . ? C21A N21A C25A 123.4(12) . . ? C23A N21A C25A 110.3(15) . . ? N21A C21A O21 125.2(12) . . ? N21A C21A H21A 117.4 . . ? O21 C21A H21A 117.4 . . ? N21A C23A C24A 122.6(16) . . ? N21A C23A H23A 106.7 . . ? C24A C23A H23A 106.7 . . ? N21A C23A H23B 106.7 . . ? C24A C23A H23B 106.7 . . ? H23A C23A H23B 106.6 . . ? N21A C25A C26A 113.4(15) . . ? N21A C25A H25A 108.9 . . ? C26A C25A H25A 108.9 . . ? N21A C25A H25B 108.9 . . ? C26A C25A H25B 108.9 . . ? H25A C25A H25B 107.7 . . ? C23A C24A H24A 109.5 . . ? C23A C24A H24B 109.5 . . ? H24A C24A H24B 109.5 . . ? C23A C24A H24C 109.5 . . ? H24A C24A H24C 109.5 . . ? H24B C24A H24C 109.5 . . ? C25A C26A H26A 109.5 . . ? C25A C26A H26B 109.5 . . ? H26A C26A H26B 109.5 . . ? C25A C26A H26C 109.5 . . ? H26A C26A H26C 109.5 . . ? H26B C26A H26C 109.5 . . ? C21B N21B C25B 108(2) . . ? C21B N21B C23B 119.7(17) . . ? C25B N21B C23B 121(2) . . ? N21B C21B O21 124.3(16) . . ? N21B C21B H21B 117.9 . . ? O21 C21B H21B 117.9 . . ? N21B C23B C24B 115(3) . . ? N21B C23B H23C 108.4 . . ? C24B C23B H23C 108.4 . . ? N21B C23B H23D 108.4 . . ? C24B C23B H23D 108.4 . . ? H23C C23B H23D 107.5 . . ? N21B C25B C26B 98(2) . . ? N21B C25B H25C 112.2 . . ? C26B C25B H25C 112.2 . . ? N21B C25B H25D 112.2 . . ? C26B C25B H25D 112.2 . . ? H25C C25B H25D 109.8 . . ? C23B C24B H24D 109.5 . . ? C23B C24B H24E 109.5 . . ? H24D C24B H24E 109.5 . . ? C23B C24B H24F 109.5 . . ? H24D C24B H24F 109.5 . . ? H24E C24B H24F 109.5 . . ? C25B C26B H26D 109.5 . . ? C25B C26B H26E 109.5 . . ? H26D C26B H26E 109.5 . . ? C25B C26B H26F 109.5 . . ? H26D C26B H26F 109.5 . . ? H26E C26B H26F 109.5 . . ? O1 Ni1 O1 89.9(3) . 5 ? O1 Ni1 O21 90.2(3) . 5 ? O1 Ni1 O21 88.3(3) 5 5 ? O1 Ni1 O21 88.3(3) . . ? O1 Ni1 O21 90.2(3) 5 . ? O21 Ni1 O21 177.9(5) 5 . ? O1 Ni1 O3 92.05(18) . 4_564 ? O1 Ni1 O3 177.7(2) 5 4_564 ? O21 Ni1 O3 90.5(2) 5 4_564 ? O21 Ni1 O3 91.0(3) . 4_564 ? O1 Ni1 O3 177.7(2) . 6_565 ? O1 Ni1 O3 92.05(18) 5 6_565 ? O21 Ni1 O3 91.0(3) 5 6_565 ? O21 Ni1 O3 90.5(2) . 6_565 ? O3 Ni1 O3 86.0(3) 4_564 6_565 ? C1 O1 Ni1 126.1(5) . . ? O1 C1 O2 125.2(6) . . ? O1 C1 C2 118.8(6) . . ? O2 C1 C2 115.9(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.518 _refine_diff_density_min -1.830 _refine_diff_density_rms 0.163 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.020 381 55 ' ' _platon_squeeze_details ; 1 x DEF in pore. ; # start Validation Reply Form _vrf_PLAT222_I ; PROBLEM: Large Non-Solvent H Uiso(max)/Uiso(min) .. 10.0 Ratio RESPONSE: H-atoms in question are attached to C24 at the end of a disordered ethyl chain. ; data_p3221 _database_code_depnum_ccdc_archive 'CCDC 915131' #TrackingRef 'NiAS-DMF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena{[2,2'-dihydroxy-4,4'-dicarboxylato-bis(dimethylformamido)-nickel(II)] DMF-solvate} ; _chemical_name_common ; catena((2,2'-dihydroxy-4,4'-dicarboxylato- bis(dimethylformamido)-nickel(ii)) DMF-solvate) ; _chemical_melting_point N/A _chemical_formula_moiety 'C20 H20 N2 Ni O8' _chemical_formula_sum 'C20 H20 N2 Ni O8' _chemical_formula_weight 475.09 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 31 2 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'x-y, -y, -z+2/3' '-x, -x+y, -z+1/3' 'y, x, -z' _cell_length_a 17.2139(3) _cell_length_b 17.2139(3) _cell_length_c 8.5240(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2187.42(14) _cell_formula_units_Z 3 _cell_measurement_temperature 150.0 _cell_measurement_reflns_used 4817 _cell_measurement_theta_min 2.7271 _cell_measurement_theta_max 29.2531 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.082 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 738 _exptl_absorpt_coefficient_mu 0.701 _exptl_absorpt_correction_T_min 0.57629 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1695 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14078 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_unetI/netI 0.0384 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 26.98 _reflns_number_total 3165 _reflns_number_gt 2783 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SIR-92 (Altomare 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND 3.2g (Crystal Impact 2012)' _computing_publication_material 'SHELXS-97 (Sheldrick, 2008)' _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^ > 2\s(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. DMF and phenyl hydrogens were fixed in geometrically caluclated positions and refined in riding mode. DMF methyl hydrogens were fixed in calculated positions for a two-fold staggering and refined in riding mode. The hydroxyl O-H proton on the diol could be seen in the diference maps, but free refinement of the position with a fixed O-H distance resulted in a nonsensical position. ; _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^)+(0.0744P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.013(17) _refine_ls_number_reflns 3165 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1185 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 Ni1 Ni 0.52534(3) 0.0000 0.3333 0.02594(16) Uani 1 2 d S . . O2 O 0.62765(12) 0.18497(13) 0.5293(3) 0.0284(5) Uani 1 1 d . . . O3 O 0.92332(12) 0.40055(11) 0.7709(2) 0.0220(4) Uani 1 1 d . . . O1 O 0.64884(13) 0.07749(14) 0.4265(3) 0.0356(6) Uani 1 1 d . . . O21 O 0.56368(15) 0.08383(14) 0.1361(3) 0.0370(6) Uani 1 1 d . . . C2 C 0.77184(18) 0.19918(18) 0.5485(3) 0.0224(6) Uani 1 1 d . . . C4 C 0.80392(18) 0.27782(18) 0.6362(3) 0.0227(6) Uani 1 1 d . . . H4 H 0.7655 0.2991 0.6628 0.027 Uiso 1 1 calc R . . C7 C 0.95208(18) 0.29400(18) 0.6417(4) 0.0232(6) Uani 1 1 d . . . C3 C 0.8289(2) 0.16683(19) 0.5096(4) 0.0318(7) Uani 1 1 d . . . H3 H 0.8075 0.1140 0.4526 0.038 Uiso 1 1 calc R . . N21 N 0.5292(2) 0.14975(19) -0.0626(3) 0.0453(8) Uani 1 1 d . . . C6 C 0.89293(18) 0.32433(16) 0.6836(3) 0.0219(5) Uani 1 1 d . . . C5 C 0.9181(2) 0.2141(2) 0.5565(4) 0.0351(8) Uani 1 1 d . . . H5 H 0.9561 0.1921 0.5307 0.042 Uiso 1 1 calc R . . C1 C 0.67590(18) 0.14948(18) 0.4977(3) 0.0245(6) Uani 1 1 d . . . C21 C 0.5100(3) 0.0855(2) 0.0384(4) 0.0398(8) Uani 1 1 d . . . H21 H 0.4517 0.0371 0.0380 0.048 Uiso 1 1 calc R . . C23 C 0.4616(3) 0.1499(3) -0.1649(5) 0.0538(10) Uani 1 1 d . . . H23A H 0.4889 0.2024 -0.2300 0.081 Uiso 0.50 1 calc PR . . H23B H 0.4153 0.1501 -0.1023 0.081 Uiso 0.50 1 calc PR . . H23C H 0.4360 0.0972 -0.2297 0.081 Uiso 0.50 1 calc PR . . H23D H 0.4046 0.0974 -0.1447 0.081 Uiso 0.50 1 calc PR . . H23E H 0.4781 0.1497 -0.2724 0.081 Uiso 0.50 1 calc PR . . H23F H 0.4575 0.2026 -0.1450 0.081 Uiso 0.50 1 calc PR . . C22 C 0.6175(3) 0.2301(3) -0.0621(5) 0.0591(11) Uani 1 1 d . . . H22A H 0.6203 0.2700 -0.1435 0.089 Uiso 0.50 1 calc PR . . H22B H 0.6625 0.2138 -0.0801 0.089 Uiso 0.50 1 calc PR . . H22C H 0.6277 0.2596 0.0377 0.089 Uiso 0.50 1 calc PR . . H22D H 0.6534 0.2256 0.0196 0.089 Uiso 0.50 1 calc PR . . H22E H 0.6112 0.2818 -0.0439 0.089 Uiso 0.50 1 calc PR . . H22F H 0.6460 0.2360 -0.1616 0.089 Uiso 0.50 1 calc PR . . 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 Ni1 0.01235(19) 0.0128(3) 0.0528(3) -0.0072(2) -0.00360(12) 0.00639(13) O2 0.0165(10) 0.0199(10) 0.0517(12) -0.0089(9) -0.0063(9) 0.0113(8) O3 0.0143(9) 0.0107(8) 0.0393(10) 0.0000(8) 0.0002(8) 0.0048(7) O1 0.0159(9) 0.0247(11) 0.0683(16) -0.0187(10) -0.0102(10) 0.0117(9) O21 0.0243(11) 0.0197(10) 0.0591(14) -0.0019(10) 0.0119(11) 0.0051(9) C2 0.0150(13) 0.0118(12) 0.0384(15) -0.0013(11) -0.0005(11) 0.0053(11) C4 0.0134(12) 0.0144(13) 0.0427(17) 0.0017(12) 0.0020(11) 0.0087(11) C7 0.0119(13) 0.0145(13) 0.0428(16) 0.0003(12) -0.0047(12) 0.0062(11) C3 0.0203(14) 0.0185(13) 0.0569(18) -0.0132(12) -0.0052(13) 0.0100(11) N21 0.0514(19) 0.0272(15) 0.0468(17) 0.0042(13) 0.0087(14) 0.0117(14) C6 0.0163(13) 0.0120(11) 0.0367(14) -0.0013(10) -0.0010(12) 0.0067(11) C5 0.0189(14) 0.0213(15) 0.066(2) -0.0081(14) -0.0014(14) 0.0110(12) C1 0.0185(14) 0.0149(13) 0.0403(17) -0.0040(11) -0.0050(12) 0.0085(12) C21 0.0359(19) 0.0280(17) 0.052(2) 0.0011(16) 0.0120(17) 0.0135(15) C23 0.067(3) 0.053(2) 0.045(2) -0.0008(18) -0.001(2) 0.033(2) C22 0.056(3) 0.033(2) 0.068(3) 0.0149(19) 0.021(2) 0.0072(18) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Ni1 O1 2.023(2) 4 ? Ni1 O1 2.023(2) . ? Ni1 O3 2.0761(18) 6_546 ? Ni1 O3 2.0761(18) 3_664 ? Ni1 O21 2.096(2) . ? Ni1 O21 2.096(2) 4 ? O2 C1 1.282(3) . ? O3 C6 1.365(3) . ? O3 Ni1 2.0761(18) 2_655 ? O1 C1 1.243(3) . ? O21 C21 1.256(4) . ? C2 C3 1.389(4) . ? C2 C4 1.396(4) . ? C2 C1 1.495(4) . ? C4 C6 1.388(4) . ? C4 H4 0.9300 . ? C7 C5 1.399(4) . ? C7 C6 1.403(4) . ? C7 C7 1.491(5) 5_766 ? C3 C5 1.390(4) . ? C3 H3 0.9300 . ? N21 C21 1.306(5) . ? N21 C23 1.455(5) . ? N21 C22 1.456(5) . ? C5 H5 0.9300 . ? C21 H21 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C23 H23D 0.9600 . ? C23 H23E 0.9600 . ? C23 H23F 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C22 H22D 0.9600 . ? C22 H22E 0.9600 . ? C22 H22F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ni1 O1 87.70(11) 4 . ? O1 Ni1 O3 91.98(7) 4 6_546 ? O1 Ni1 O3 177.64(9) . 6_546 ? O1 Ni1 O3 177.64(9) 4 3_664 ? O1 Ni1 O3 91.98(7) . 3_664 ? O3 Ni1 O3 88.43(10) 6_546 3_664 ? O1 Ni1 O21 92.68(9) 4 . ? O1 Ni1 O21 89.74(9) . . ? O3 Ni1 O21 87.93(8) 6_546 . ? O3 Ni1 O21 89.66(8) 3_664 . ? O1 Ni1 O21 89.74(9) 4 4 ? O1 Ni1 O21 92.68(9) . 4 ? O3 Ni1 O21 89.66(8) 6_546 4 ? O3 Ni1 O21 87.93(8) 3_664 4 ? O21 Ni1 O21 176.64(13) . 4 ? C6 O3 Ni1 120.07(16) . 2_655 ? C1 O1 Ni1 126.55(18) . . ? C21 O21 Ni1 124.5(2) . . ? C3 C2 C4 120.0(3) . . ? C3 C2 C1 120.1(2) . . ? C4 C2 C1 119.9(2) . . ? C6 C4 C2 120.2(2) . . ? C6 C4 H4 119.9 . . ? C2 C4 H4 119.9 . . ? C5 C7 C6 118.3(3) . . ? C5 C7 C7 119.7(2) . 5_766 ? C6 C7 C7 122.0(2) . 5_766 ? C2 C3 C5 119.5(3) . . ? C2 C3 H3 120.2 . . ? C5 C3 H3 120.2 . . ? C21 N21 C23 122.1(3) . . ? C21 N21 C22 120.3(4) . . ? C23 N21 C22 117.1(3) . . ? O3 C6 C4 119.7(2) . . ? O3 C6 C7 119.7(2) . . ? C4 C6 C7 120.6(2) . . ? C3 C5 C7 121.4(3) . . ? C3 C5 H5 119.3 . . ? C7 C5 H5 119.3 . . ? O1 C1 O2 124.7(2) . . ? O1 C1 C2 117.9(2) . . ? O2 C1 C2 117.4(2) . . ? O21 C21 N21 125.3(3) . . ? O21 C21 H21 117.3 . . ? N21 C21 H21 117.3 . . ? N21 C23 H23A 109.5 . . ? N21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N21 C23 H23D 109.5 . . ? H23A C23 H23D 141.1 . . ? H23B C23 H23D 56.3 . . ? H23C C23 H23D 56.3 . . ? N21 C23 H23E 109.5 . . ? H23A C23 H23E 56.3 . . ? H23B C23 H23E 141.1 . . ? H23C C23 H23E 56.3 . . ? H23D C23 H23E 109.5 . . ? N21 C23 H23F 109.5 . . ? H23A C23 H23F 56.3 . . ? H23B C23 H23F 56.3 . . ? H23C C23 H23F 141.1 . . ? H23D C23 H23F 109.5 . . ? H23E C23 H23F 109.5 . . ? N21 C22 H22A 109.5 . . ? N21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N21 C22 H22D 109.5 . . ? H22A C22 H22D 141.1 . . ? H22B C22 H22D 56.3 . . ? H22C C22 H22D 56.3 . . ? N21 C22 H22E 109.5 . . ? H22A C22 H22E 56.3 . . ? H22B C22 H22E 141.1 . . ? H22C C22 H22E 56.3 . . ? H22D C22 H22E 109.5 . . ? N21 C22 H22F 109.5 . . ? H22A C22 H22F 56.3 . . ? H22B C22 H22F 56.3 . . ? H22C C22 H22F 141.1 . . ? H22D C22 H22F 109.5 . . ? H22E C22 H22F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.98 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.851 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.068 # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.032 789 128 '3 x DMF' _platon_squeeze_details ; ;