# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef '- CrystEngComm_cif_deposit_all.cif' #=============================================================================# _publ_contact_author ; 'Cindri\'c, Marina' Department of Chemistry, Laboratory of General and Inorganic Chemistry Faculty of Science, University of Zagreb Horvatovac 102a, HR-10000 Zagreb, Croatia ; _publ_contact_author_phone '++385 1 4606-351' _publ_contact_author_fax '++385 1 461 1191' _publ_contact_author_email marina@chem.pmf.hr _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter ; November, 30, 2011 Dear Lady or Sir, Please consider this three structures for deposition at CCDC. Structures will be published in Cryst.Eng.Comm. Many thanks. Sincerely yours, Prof. Marina Cindri\'c. ; #=============================================================================# _publ_section_title ; Three routes in the preparation of nickel(II) salicylaldehyde 4-phenyl and 4-methylthiosemicarbazonato complexes: Mechanochemical versus Electrochemical and Conventional approach ; loop_ _publ_author_name _publ_author_address M.Cindric ; Department of Chemistry, Laboratory of General and Inorganic Chemistry Faculty of Science, University of Zagreb Horvatovac 102a, HR-10000 Zagreb, Croatia ; M.Uzelac ; Department of Chemistry, Laboratory of General and Inorganic Chemistry Faculty of Science, University of Zagreb Horvatovac 102a, HR-10000 Zagreb, Croatia ; D.Cincic ; Department of Chemistry, Laboratory of General and Inorganic Chemistry Faculty of Science, University of Zagreb Horvatovac 102a, HR-10000 Zagreb, Croatia ; I.Halasz ; Department of Chemistry, Laboratory of Organic Chemistry Faculty of Science, University of Zagreb Horvatovac 102a, HR-10000 Zagreb, Croatia ; G.Pavlovic ; Faculty of Textile Technology, Department of Applied Chemistry Laboratory of General Chemistry, University of Zagreb, Prilaz baruna Filipovi\'ca 28a HR-10000 Zagreb, Croatia ; T.Hrenar ; Department of Chemistry, Laboratory of Physical Chemistry Faculty of Science, University of Zagreb Horvatovac 102a, HR-10000 Zagreb, Croatia ; M.Curic ; Rudjer Bo\2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.Version 1.171.34.44' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.Version 1.171.34.44' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.Version 1.171.34.44' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 for Windows, Ver. 1.70.01 (Farrugia, 2005), MERCURY 1.4.2 (CCDC, 2006) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; ? ; _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^)+(0.0419P)^2^+13.3209P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5004 _refine_ls_number_parameters 377 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1694 _refine_ls_R_factor_gt 0.0914 _refine_ls_wR_factor_ref 0.1926 _refine_ls_wR_factor_gt 0.1682 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.26590(5) 0.63615(5) 0.71973(13) 0.0347(3) Uani 1 1 d . . . S1 S 0.33254(10) 0.56623(10) 0.8849(3) 0.0410(5) Uani 1 1 d . . . S2 S 0.36190(10) 0.70162(10) 0.7157(3) 0.0467(6) Uani 1 1 d . . . O1 O 0.2091(3) 0.6994(3) 0.5811(7) 0.0414(13) Uani 1 1 d . . . O2 O 0.2816(3) 1.0047(3) 0.9248(9) 0.0603(16) Uani 1 1 d D . . O3 O 0.4155(4) 0.4663(4) 1.2675(10) 0.084(2) Uani 1 1 d D . . H1O3 H 0.403(6) 0.451(6) 1.354(9) 0.101 Uiso 1 1 d D . . N1 N 0.1951(3) 0.5689(3) 0.7259(8) 0.0359(15) Uani 1 1 d . . . N2 N 0.2055(3) 0.5056(3) 0.8178(8) 0.0384(15) Uani 1 1 d . . . N3 N 0.2907(3) 0.4437(3) 0.9969(8) 0.0420(16) Uani 1 1 d . . . H3N H 0.3337 0.4447 1.0444 0.050 Uiso 1 1 calc R . . N4 N 0.3940(3) 0.8399(3) 0.7632(9) 0.0463(18) Uani 1 1 d . . . H4N H 0.3793 0.8832 0.7528 0.056 Uiso 1 1 calc R . . N5 N 0.2788(3) 0.8136(3) 0.7149(9) 0.0462(17) Uani 1 1 d . . . H5N H 0.2453 0.7849 0.6776 0.055 Uiso 1 1 calc R . . N6 N 0.2636(3) 0.8823(3) 0.7537(9) 0.0427(16) Uani 1 1 d . . . C1 C 0.1438(5) 0.6917(4) 0.5106(10) 0.0418(19) Uani 1 1 d . . . C2 C 0.1036(4) 0.6311(4) 0.5350(9) 0.0377(17) Uani 1 1 d . . . C3 C 0.0338(4) 0.6261(4) 0.4539(10) 0.045(2) Uani 1 1 d . . . H3 H 0.0083 0.5854 0.4706 0.054 Uiso 1 1 calc R . . C4 C 0.0025(5) 0.6786(5) 0.3521(12) 0.063(3) Uani 1 1 d . . . H4 H -0.0441 0.6753 0.3021 0.075 Uiso 1 1 calc R . . C5 C 0.0435(5) 0.7385(5) 0.3251(12) 0.062(3) Uani 1 1 d . . . H5 H 0.0236 0.7745 0.2529 0.075 Uiso 1 1 calc R . . C6 C 0.1115(5) 0.7454(4) 0.4017(11) 0.048(2) Uani 1 1 d . . . H6 H 0.1367 0.7859 0.3817 0.058 Uiso 1 1 calc R . . C7 C 0.1316(4) 0.5742(4) 0.6418(10) 0.042(2) Uani 1 1 d . . . H7 H 0.1015 0.5366 0.6533 0.051 Uiso 1 1 calc R . . C8 C 0.2692(4) 0.5011(4) 0.8960(9) 0.0358(18) Uani 1 1 d . . . C9 C 0.2530(4) 0.3835(4) 1.0345(10) 0.0377(19) Uani 1 1 d . . . C10 C 0.1839(4) 0.3695(4) 0.9695(10) 0.0442(19) Uani 1 1 d . . . H10 H 0.1587 0.4010 0.8930 0.053 Uiso 1 1 calc R . . C11 C 0.1522(5) 0.3083(4) 1.0184(11) 0.051(2) Uani 1 1 d . . . H11 H 0.1055 0.2999 0.9751 0.061 Uiso 1 1 calc R . . C12 C 0.1876(5) 0.2603(4) 1.1280(11) 0.049(2) Uani 1 1 d . . . H12 H 0.1658 0.2191 1.1580 0.058 Uiso 1 1 calc R . . C13 C 0.2554(5) 0.2740(4) 1.1925(11) 0.054(2) Uani 1 1 d . . . H13 H 0.2795 0.2423 1.2704 0.065 Uiso 1 1 calc R . . C14 C 0.2899(5) 0.3338(4) 1.1459(11) 0.050(2) Uani 1 1 d . . . H14 H 0.3369 0.3409 1.1881 0.060 Uiso 1 1 calc R . . C15 C 0.3441(4) 0.7905(4) 0.7338(10) 0.0379(18) Uani 1 1 d . . . C16 C 0.1988(4) 0.9013(4) 0.7061(11) 0.044(2) Uani 1 1 d . . . H16 H 0.1682 0.8700 0.6412 0.053 Uiso 1 1 calc R . . C17 C 0.2140(4) 1.0175(4) 0.8619(11) 0.046(2) Uani 1 1 d . . . C18 C 0.1737(4) 0.9699(4) 0.7520(11) 0.044(2) Uani 1 1 d . . . C19 C 0.1050(5) 0.9874(4) 0.6930(11) 0.054(2) Uani 1 1 d . . . H19 H 0.0772 0.9561 0.6209 0.065 Uiso 1 1 calc R . . C20 C 0.0767(5) 1.0509(5) 0.7395(14) 0.063(3) Uani 1 1 d . . . H20 H 0.0305 1.0624 0.6978 0.076 Uiso 1 1 calc R . . C21 C 0.1172(5) 1.0965(5) 0.8471(14) 0.064(3) Uani 1 1 d . . . H21 H 0.0984 1.1392 0.8781 0.077 Uiso 1 1 calc R . . C22 C 0.1844(5) 1.0803(4) 0.9091(12) 0.057(2) Uani 1 1 d . . . H22 H 0.2110 1.1115 0.9839 0.069 Uiso 1 1 calc R . . C23 C 0.4672(4) 0.8325(4) 0.8088(10) 0.0382(18) Uani 1 1 d . . . C24 C 0.4980(4) 0.7812(4) 0.9242(11) 0.050(2) Uani 1 1 d . . . H24 H 0.4707 0.7473 0.9677 0.060 Uiso 1 1 calc R . . C25 C 0.5693(5) 0.7814(5) 0.9727(13) 0.060(3) Uani 1 1 d . . . H25 H 0.5901 0.7463 1.0463 0.072 Uiso 1 1 calc R . . C26 C 0.6102(5) 0.8319(5) 0.9152(13) 0.062(3) Uani 1 1 d . . . H26 H 0.6582 0.8319 0.9521 0.075 Uiso 1 1 calc R . . C27 C 0.5806(5) 0.8825(5) 0.8032(14) 0.066(3) Uani 1 1 d . . . H27 H 0.6085 0.9171 0.7639 0.079 Uiso 1 1 calc R . . C28 C 0.5091(5) 0.8825(4) 0.7481(12) 0.053(2) Uani 1 1 d . . . H28 H 0.4893 0.9163 0.6697 0.063 Uiso 1 1 calc R . . C29 C 0.4800(6) 0.4313(6) 1.2612(19) 0.102(4) Uani 1 1 d . . . H29A H 0.5133 0.4447 1.3586 0.153 Uiso 1 1 calc R . . H29B H 0.4973 0.4450 1.1594 0.153 Uiso 1 1 calc R . . H29C H 0.4731 0.3807 1.2613 0.153 Uiso 1 1 calc R . . H1O2 H 0.291(6) 0.965(3) 0.891(15) 0.122 Uiso 1 1 d 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 Ni1 0.0249(5) 0.0378(5) 0.0415(6) 0.0009(5) 0.0055(4) 0.0020(4) S1 0.0283(11) 0.0435(10) 0.0500(13) 0.0029(9) 0.0025(10) -0.0027(8) S2 0.0249(11) 0.0412(10) 0.0745(16) 0.0043(10) 0.0100(11) 0.0025(8) O1 0.027(3) 0.048(3) 0.048(3) 0.007(3) 0.001(3) -0.004(2) O2 0.049(4) 0.060(4) 0.070(4) -0.001(3) 0.007(4) -0.004(3) O3 0.056(5) 0.111(6) 0.083(6) 0.028(5) 0.007(4) -0.013(4) N1 0.032(4) 0.039(3) 0.041(4) 0.000(3) 0.019(3) 0.006(3) N2 0.022(3) 0.043(3) 0.048(4) 0.008(3) -0.002(3) 0.001(3) N3 0.025(4) 0.045(4) 0.052(4) 0.005(3) -0.004(3) 0.000(3) N4 0.033(4) 0.034(3) 0.072(5) 0.010(3) 0.007(4) 0.001(3) N5 0.024(4) 0.039(3) 0.075(5) 0.003(3) 0.007(4) -0.005(3) N6 0.034(4) 0.037(3) 0.058(5) 0.009(3) 0.010(4) -0.001(3) C1 0.045(5) 0.047(4) 0.033(4) 0.001(4) 0.004(4) 0.009(4) C2 0.036(5) 0.046(4) 0.031(4) -0.002(4) 0.008(4) 0.004(4) C3 0.020(4) 0.066(5) 0.048(5) 0.006(4) 0.001(4) 0.000(4) C4 0.027(5) 0.101(7) 0.058(6) 0.013(5) 0.001(5) 0.018(5) C5 0.055(6) 0.079(6) 0.054(6) 0.022(5) 0.008(6) 0.015(5) C6 0.043(5) 0.056(5) 0.047(5) 0.008(4) 0.007(5) -0.001(4) C7 0.029(5) 0.046(4) 0.052(5) -0.009(4) 0.008(4) -0.005(4) C8 0.039(5) 0.034(4) 0.037(4) -0.001(3) 0.010(4) 0.003(3) C9 0.041(5) 0.034(4) 0.039(5) 0.000(3) 0.011(4) 0.003(3) C10 0.039(5) 0.048(4) 0.041(5) 0.005(4) -0.007(4) -0.005(4) C11 0.049(6) 0.053(5) 0.048(5) 0.001(4) 0.001(5) -0.014(4) C12 0.054(6) 0.043(4) 0.048(5) 0.004(4) 0.007(5) -0.010(4) C13 0.064(7) 0.046(5) 0.051(6) 0.005(4) 0.009(5) 0.006(4) C14 0.038(5) 0.047(4) 0.064(6) 0.000(4) 0.007(5) 0.000(4) C15 0.024(4) 0.042(4) 0.047(5) 0.010(4) 0.002(4) 0.003(3) C16 0.035(5) 0.048(4) 0.052(5) 0.010(4) 0.011(4) -0.001(4) C17 0.028(5) 0.056(5) 0.055(6) 0.014(4) 0.008(5) -0.001(4) C18 0.031(5) 0.049(4) 0.052(5) 0.016(4) 0.009(4) 0.007(4) C19 0.053(6) 0.054(5) 0.056(6) 0.008(4) 0.011(5) 0.007(4) C20 0.035(5) 0.064(6) 0.094(8) 0.009(6) 0.020(6) 0.019(4) C21 0.064(7) 0.048(5) 0.088(8) 0.004(5) 0.037(7) 0.009(5) C22 0.062(7) 0.047(5) 0.069(6) 0.000(4) 0.028(6) -0.001(4) C23 0.021(4) 0.042(4) 0.053(5) -0.002(4) 0.010(4) 0.001(3) C24 0.039(5) 0.052(5) 0.058(6) 0.006(4) 0.006(5) -0.001(4) C25 0.040(6) 0.062(6) 0.072(7) -0.005(5) -0.009(5) 0.003(4) C26 0.032(5) 0.072(6) 0.080(7) -0.009(6) 0.002(5) -0.002(5) C27 0.046(6) 0.069(6) 0.085(8) -0.002(5) 0.017(6) -0.013(5) C28 0.040(5) 0.051(5) 0.066(6) 0.014(4) 0.007(5) -0.008(4) C29 0.055(7) 0.090(8) 0.154(13) 0.024(8) -0.004(8) 0.010(6) _geom_special_details ; ? ; 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 1.858(5) . ? Ni1 N1 1.871(6) . ? Ni1 S1 2.139(2) . ? Ni1 S2 2.234(2) . ? S1 C8 1.744(7) . ? S2 C15 1.712(7) . ? O1 C1 1.308(9) . ? O2 C17 1.348(10) . ? O2 H1O2 0.83(2) . ? O3 C29 1.420(12) . ? O3 H1O3 0.82(2) . ? N1 C7 1.308(10) . ? N1 N2 1.393(8) . ? N2 C8 1.295(9) . ? N3 C8 1.368(9) . ? N3 C9 1.402(9) . ? N3 H3N 0.8600 . ? N4 C15 1.333(9) . ? N4 C23 1.414(9) . ? N4 H4N 0.8600 . ? N5 C15 1.324(9) . ? N5 N6 1.369(8) . ? N5 H5N 0.8600 . ? N6 C16 1.302(10) . ? C1 C2 1.409(10) . ? C1 C6 1.409(11) . ? C2 C3 1.406(10) . ? C2 C7 1.417(10) . ? C3 C4 1.356(11) . ? C3 H3 0.9300 . ? C4 C5 1.412(12) . ? C4 H4 0.9300 . ? C5 C6 1.368(12) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 C10 1.383(10) . ? C9 C14 1.401(11) . ? C10 C11 1.385(10) . ? C10 H10 0.9300 . ? C11 C12 1.362(11) . ? C11 H11 0.9300 . ? C12 C13 1.357(12) . ? C12 H12 0.9300 . ? C13 C14 1.386(11) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C16 C18 1.444(10) . ? C16 H16 0.9300 . ? C17 C22 1.388(11) . ? C17 C18 1.398(11) . ? C18 C19 1.380(11) . ? C19 C20 1.386(11) . ? C19 H19 0.9300 . ? C20 C21 1.368(13) . ? C20 H20 0.9300 . ? C21 C22 1.351(13) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C28 1.378(10) . ? C23 C24 1.397(11) . ? C24 C25 1.374(12) . ? C24 H24 0.9300 . ? C25 C26 1.360(12) . ? C25 H25 0.9300 . ? C26 C27 1.365(13) . ? C26 H26 0.9300 . ? C27 C28 1.386(12) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 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 N1 94.5(2) . . ? O1 Ni1 S1 178.08(18) . . ? N1 Ni1 S1 86.8(2) . . ? O1 Ni1 S2 93.26(16) . . ? N1 Ni1 S2 170.90(19) . . ? S1 Ni1 S2 85.59(8) . . ? C8 S1 Ni1 95.7(3) . . ? C15 S2 Ni1 110.7(3) . . ? C1 O1 Ni1 128.7(5) . . ? C17 O2 H1O2 107(9) . . ? C29 O3 H1O3 104(9) . . ? C7 N1 N2 112.4(6) . . ? C7 N1 Ni1 124.7(5) . . ? N2 N1 Ni1 122.9(5) . . ? C8 N2 N1 110.8(6) . . ? C8 N3 C9 129.8(7) . . ? C8 N3 H3N 115.1 . . ? C9 N3 H3N 115.1 . . ? C15 N4 C23 130.3(6) . . ? C15 N4 H4N 114.9 . . ? C23 N4 H4N 114.9 . . ? C15 N5 N6 121.3(6) . . ? C15 N5 H5N 119.3 . . ? N6 N5 H5N 119.3 . . ? C16 N6 N5 115.1(7) . . ? O1 C1 C2 123.3(7) . . ? O1 C1 C6 119.3(7) . . ? C2 C1 C6 117.4(8) . . ? C3 C2 C1 120.3(7) . . ? C3 C2 C7 118.3(7) . . ? C1 C2 C7 121.5(7) . . ? C4 C3 C2 122.1(8) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? C3 C4 C5 117.4(8) . . ? C3 C4 H4 121.3 . . ? C5 C4 H4 121.3 . . ? C6 C5 C4 122.2(8) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C5 C6 C1 120.6(8) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? N1 C7 C2 127.2(7) . . ? N1 C7 H7 116.4 . . ? C2 C7 H7 116.4 . . ? N2 C8 N3 120.7(7) . . ? N2 C8 S1 123.7(6) . . ? N3 C8 S1 115.5(6) . . ? C10 C9 C14 118.5(7) . . ? C10 C9 N3 125.4(7) . . ? C14 C9 N3 116.2(7) . . ? C9 C10 C11 119.9(7) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 121.8(8) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C13 C12 C11 118.4(8) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C12 C13 C14 122.0(8) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C13 C14 C9 119.3(8) . . ? C13 C14 H14 120.3 . . ? C9 C14 H14 120.3 . . ? N5 C15 N4 116.5(6) . . ? N5 C15 S2 120.7(6) . . ? N4 C15 S2 122.8(6) . . ? N6 C16 C18 121.2(8) . . ? N6 C16 H16 119.4 . . ? C18 C16 H16 119.4 . . ? O2 C17 C22 118.0(8) . . ? O2 C17 C18 122.2(7) . . ? C22 C17 C18 119.9(8) . . ? C19 C18 C17 118.3(8) . . ? C19 C18 C16 118.2(8) . . ? C17 C18 C16 123.4(8) . . ? C18 C19 C20 121.0(9) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C21 C20 C19 119.5(9) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C22 C21 C20 120.8(8) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C21 C22 C17 120.5(9) . . ? C21 C22 H22 119.8 . . ? C17 C22 H22 119.8 . . ? C28 C23 C24 119.0(7) . . ? C28 C23 N4 117.8(7) . . ? C24 C23 N4 122.9(7) . . ? C25 C24 C23 119.3(8) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C26 C25 C24 121.4(9) . . ? C26 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C25 C26 C27 119.9(9) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C26 C27 C28 120.1(8) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C23 C28 C27 120.4(8) . . ? C23 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? O3 C29 H29A 109.5 . . ? O3 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O3 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 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 O1 Ni1 S1 C8 132(5) . . . . ? N1 Ni1 S1 C8 0.2(3) . . . . ? S2 Ni1 S1 C8 -174.8(2) . . . . ? O1 Ni1 S2 C15 41.5(3) . . . . ? N1 Ni1 S2 C15 -170.4(13) . . . . ? S1 Ni1 S2 C15 -137.0(3) . . . . ? N1 Ni1 O1 C1 -3.7(6) . . . . ? S1 Ni1 O1 C1 -135(5) . . . . ? S2 Ni1 O1 C1 171.5(6) . . . . ? O1 Ni1 N1 C7 3.3(6) . . . . ? S1 Ni1 N1 C7 -178.1(6) . . . . ? S2 Ni1 N1 C7 -144.8(11) . . . . ? O1 Ni1 N1 N2 -178.9(5) . . . . ? S1 Ni1 N1 N2 -0.3(5) . . . . ? S2 Ni1 N1 N2 33.0(16) . . . . ? C7 N1 N2 C8 178.4(6) . . . . ? Ni1 N1 N2 C8 0.4(8) . . . . ? C15 N5 N6 C16 170.2(7) . . . . ? Ni1 O1 C1 C2 2.1(11) . . . . ? Ni1 O1 C1 C6 -176.6(5) . . . . ? O1 C1 C2 C3 -179.4(7) . . . . ? C6 C1 C2 C3 -0.7(11) . . . . ? O1 C1 C2 C7 1.1(11) . . . . ? C6 C1 C2 C7 179.8(7) . . . . ? C1 C2 C3 C4 -0.8(12) . . . . ? C7 C2 C3 C4 178.8(8) . . . . ? C2 C3 C4 C5 2.1(13) . . . . ? C3 C4 C5 C6 -2.1(14) . . . . ? C4 C5 C6 C1 0.7(14) . . . . ? O1 C1 C6 C5 179.5(8) . . . . ? C2 C1 C6 C5 0.7(12) . . . . ? N2 N1 C7 C2 -179.5(7) . . . . ? Ni1 N1 C7 C2 -1.6(11) . . . . ? C3 C2 C7 N1 179.1(7) . . . . ? C1 C2 C7 N1 -1.3(12) . . . . ? N1 N2 C8 N3 178.8(6) . . . . ? N1 N2 C8 S1 -0.2(9) . . . . ? C9 N3 C8 N2 0.0(12) . . . . ? C9 N3 C8 S1 179.0(6) . . . . ? Ni1 S1 C8 N2 0.0(7) . . . . ? Ni1 S1 C8 N3 -179.0(5) . . . . ? C8 N3 C9 C10 1.8(12) . . . . ? C8 N3 C9 C14 -179.0(7) . . . . ? C14 C9 C10 C11 1.6(11) . . . . ? N3 C9 C10 C11 -179.2(7) . . . . ? C9 C10 C11 C12 -1.0(12) . . . . ? C10 C11 C12 C13 1.1(13) . . . . ? C11 C12 C13 C14 -2.1(13) . . . . ? C12 C13 C14 C9 2.8(13) . . . . ? C10 C9 C14 C13 -2.5(11) . . . . ? N3 C9 C14 C13 178.2(7) . . . . ? N6 N5 C15 N4 -11.3(11) . . . . ? N6 N5 C15 S2 170.1(6) . . . . ? C23 N4 C15 N5 171.4(8) . . . . ? C23 N4 C15 S2 -10.1(13) . . . . ? Ni1 S2 C15 N5 -13.1(8) . . . . ? Ni1 S2 C15 N4 168.5(6) . . . . ? N5 N6 C16 C18 174.2(6) . . . . ? O2 C17 C18 C19 -179.7(7) . . . . ? C22 C17 C18 C19 0.2(12) . . . . ? O2 C17 C18 C16 4.6(12) . . . . ? C22 C17 C18 C16 -175.5(7) . . . . ? N6 C16 C18 C19 178.1(8) . . . . ? N6 C16 C18 C17 -6.2(12) . . . . ? C17 C18 C19 C20 0.8(12) . . . . ? C16 C18 C19 C20 176.7(8) . . . . ? C18 C19 C20 C21 -0.8(13) . . . . ? C19 C20 C21 C22 -0.3(14) . . . . ? C20 C21 C22 C17 1.3(14) . . . . ? O2 C17 C22 C21 178.7(8) . . . . ? C18 C17 C22 C21 -1.3(13) . . . . ? C15 N4 C23 C28 146.3(9) . . . . ? C15 N4 C23 C24 -39.8(13) . . . . ? C28 C23 C24 C25 -0.7(12) . . . . ? N4 C23 C24 C25 -174.5(8) . . . . ? C23 C24 C25 C26 2.3(14) . . . . ? C24 C25 C26 C27 -1.9(15) . . . . ? C25 C26 C27 C28 -0.1(15) . . . . ? C24 C23 C28 C27 -1.1(13) . . . . ? N4 C23 C28 C27 173.0(8) . . . . ? C26 C27 C28 C23 1.6(14) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.596 _refine_diff_density_min -0.649 _refine_diff_density_rms 0.113 data_phenyl _database_code_depnum_ccdc_archive 'CCDC 856627' #TrackingRef '- CrystEngComm_cif_deposit_all.cif' _cell_length_a 11.87650(54) _cell_length_b 22.5378(12) _cell_length_c 10.78016(51) _cell_angle_alpha 90 _cell_angle_beta 116.1741(29) _cell_angle_gamma 90 _cell_volume 2589.64(22) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _chemical_formula_moiety 'C28 H24 N6 Ni O2 S2' _chemical_formula_sum 'C28 H24 N6 Ni O2 S2' _chemical_formula_weight 599.36 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+1/2' 'x, y, z' 'x+1/2, -y+1/2, z+1/2' 'x+1/2, y+1/2, z' _diffrn_radiation_type 'Cu K\a_1' _diffrn_measurement_device_type 'Bruker D8 Advance in Debye-Scherrer geometry' _diffrn_radiation_wavelength 1.54059 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.537 _refine_ls_hydrogen_treatment refall _refine_ls_shift/su_max <0.01 _refine_ls_number_parameters 124 _pd_proc_ls_prof_R_factor 0.0349 _pd_proc_ls_prof_wR_factor 0.0448 _refine_ls_R_Fsqd_factor 0.0162 _cell_measurement_temperature 293 _diffrn_ambient_temperature 293 _exptl_crystal_description 'microcrystalline powder' _exptl_crystal_colour green _computing_data_collection Bruker _computing_data_reduction None _computing_cell_refinement TOPAS _computing_structure_solution 'simulated annealing in TOPAS' _computing_structure_refinement TOPAS loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv Ni1 Ni 4 0.5 0.23474(17) 0.75 1 3.019(98) S1 S 8 0.45997(33) 0.16691(17) 0.56874(35) 1 3.019(98) O1 O 8 0.50157(34) 0.30066(22) 0.88178(38) 1 3.019(98) N1 N 8 0.31572(47) 0.22790(26) 0.69671(49) 1 3.019(98) N2 N 8 0.23673(30) 0.19015(16) 0.59148(31) 1 3.019(98) N3 N 8 0.23162(43) 0.13412(16) 0.41224(32) 1 3.019(98) H3n H 8 0.1429(16) 0.14457(76) 0.3692(20) 1 3.019(98) C1 C 8 0.41562(26) 0.31274(25) 0.92223(39) 1 3.019(98) C2 C 8 0.28979(31) 0.29657(22) 0.85301(38) 1 3.019(98) C3 C 8 0.20682(46) 0.31912(27) 0.90209(57) 1 3.019(98) H3 H 8 0.1239(18) 0.30635(88) 0.8602(24) 1 3.019(98) C4 C 8 0.23606(37) 0.35817(26) 1.01253(59) 1 3.019(98) H4 H 8 0.1858(18) 0.37557(82) 1.0582(20) 1 3.019(98) C5 C 8 0.36255(30) 0.37526(31) 1.07403(45) 1 3.019(98) H5 H 8 0.3842(20) 0.40226(76) 1.1537(23) 1 3.019(98) C6 C 8 0.44916(34) 0.35176(26) 1.03199(44) 1 3.019(98) H6 H 8 0.5342(14) 0.36484(77) 1.0765(16) 1 3.019(98) C7 C 8 0.24896(40) 0.25550(25) 0.74181(41) 1 3.019(98) H7 H 8 0.1599(14) 0.2451(12) 0.7019(19) 1 3.019(98) C8 C 8 0.30237(28) 0.16697(15) 0.53215(33) 1 3.019(98) C9 C 8 0.24896(33) 0.08218(20) 0.34737(49) 1 3.019(98) C10 C 8 0.36822(33) 0.06085(18) 0.39505(50) 1 3.019(98) H10 H 8 0.4295(16) 0.08168(84) 0.4697(20) 1 3.019(98) C11 C 8 0.39832(38) 0.00953(17) 0.34480(42) 1 3.019(98) H11 H 8 0.4920(22) -0.0037(10) 0.3902(17) 1 3.019(98) C12 C 8 0.30703(33) -0.02135(24) 0.23531(49) 1 3.019(98) H12 H 8 0.3185(16) -0.05946(84) 0.1849(21) 1 3.019(98) C13 C 8 0.18832(36) -0.00113(18) 0.18452(49) 1 3.019(98) H13 H 8 0.1303(22) -0.02411(93) 0.1090(23) 1 3.019(98) C14 C 8 0.16043(40) 0.04931(17) 0.24125(44) 1 3.019(98) H14 H 8 0.0774(16) 0.06360(84) 0.2063(25) 1 3.019(98) H1 H 8 0.1550(15) 0.19474(78) 0.5351(18) 1 3.019(98) _vrf_ATOM006_phenyl ; PROBLEM: _atom_site_U_iso_or_equiv is missing RESPONSE: Displacement parameters are reported as Biso. The rather high value is due to temperature of data collection of 140 degrees Celsius. ; _vrf_GEOM001_phenyl ; PROBLEM: _geom_bond_atom_site_label_1 is missing RESPONSE: Bond lengths and valence angles are not calculated. ; _vrf_GEOM003_phenyl ; PROBLEM: _geom_bond_distance is missing RESPONSE: Bond lengths and valence angles are not calculated. ; _vrf_GEOM006_phenyl ; PROBLEM: _geom_angle_atom_site_label_2 is missing RESPONSE: Bond lengths and valence angles are not calculated. ; _vrf_GEOM007_phenyl ; PROBLEM: _geom_angle_atom_site_label_3 is missing RESPONSE: Bond lengths and valence angles are not calculated. ; _vrf_PLAT761_phenyl ; PROBLEM: CIF Contains no X-H Bonds ...................... ? RESPONSE: Bond lengths and valence angles are not calculated. ; _vrf_PLAT762_phenyl ; PROBLEM: CIF Contains no X-Y-H or H-Y-H Angles .......... ? RESPONSE: Bond lengths and valence angles are not calculated. ; ########################################################### data_methyl _database_code_depnum_ccdc_archive 'CCDC 856628' #TrackingRef '- CrystEngComm_cif_deposit_all.cif' _cell_length_a 19.7898(10) _cell_length_b 8.36585(34) _cell_length_c 11.79716(41) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1953.12(14) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn _chemical_formula_moiety 'C18 H20 N6 Ni O2 S2' _chemical_formula_sum 'C18 H20 N6 Ni O2 S2' _chemical_formula_weight 475.23 loop_ _symmetry_equiv_pos_as_xyz '-x, -y, -z' '-x, y, -z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' 'x, -y, z+1/2' 'x, y, z' 'x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z+1/2' _diffrn_radiation_type 'Cu K\a_1' _diffrn_measurement_device_type 'Bruker D8 Advance in Debye-Scherrer geometry' _diffrn_radiation_wavelength 1.54059 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.616 _refine_ls_hydrogen_treatment refall _refine_ls_shift/su_max <0.01 _refine_ls_number_parameters 100 _pd_proc_ls_prof_R_factor 0.0318 _pd_proc_ls_prof_wR_factor 0.0411 _refine_ls_R_Fsqd_factor 0.0186 _cell_measurement_temperature 293 _diffrn_ambient_temperature 293 _exptl_crystal_description 'microcrystalline powder' _exptl_crystal_colour green _computing_data_collection Bruker _computing_data_reduction None _computing_cell_refinement TOPAS _computing_structure_solution 'simulated annealing in TOPAS' _computing_structure_refinement TOPAS loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv Ni1 Ni 4 0 0.07689(42) -0.25 1 3.10(12) S1 S 8 -0.06245(16) 0.27727(37) -0.14782(27) 1 3.10(12) O1 O 8 0.06353(24) 0.90024(67) -0.30210(41) 1 3.10(12) N1 N 8 0.06257(21) 0.08192(76) -0.11244(36) 1 3.10(12) N2 N 8 0.04163(11) 0.15485(31) -0.01359(27) 1 3.10(12) N3 N 8 -0.04201(14) 0.32410(34) 0.06880(29) 1 3.10(12) H3n H 8 -0.02253(98) 0.3080(15) 0.1343(11) 1 3.10(12) C1 C 8 0.12710(16) 0.85915(61) -0.27144(37) 1 3.10(12) C2 C 8 0.15648(18) 0.91522(39) -0.17197(24) 1 3.10(12) C3 C 8 0.22667(19) 0.89106(75) -0.14555(33) 1 3.10(12) H3 H 8 0.2496(10) 0.9368(26) -0.0812(16) 1 3.10(12) C4 C 8 0.26586(19) 0.80637(67) -0.21865(39) 1 3.10(12) H4 H 8 0.31315(95) 0.7902(22) -0.2013(16) 1 3.10(12) C5 C 8 0.23480(23) 0.73822(86) -0.31610(42) 1 3.10(12) H5 H 8 0.26597(84) 0.6829(27) -0.3690(12) 1 3.10(12) C6 C 8 0.16498(21) 0.7581(10) -0.33880(44) 1 3.10(12) H6 H 8 0.14424(69) 0.7113(19) -0.4062(17) 1 3.10(12) C7 C 8 0.11699(17) 0.00454(55) -0.09487(37) 1 3.10(12) H7 H 8 0.13919(66) 0.0256(27) -0.0333(15) 1 3.10(12) C8 C 8 -0.01324(14) 0.24020(37) -0.02549(25) 1 3.10(12) C9 C 8 -0.08968(15) 0.43884(33) 0.07746(24) 1 3.10(12) H9a H 8 -0.08330(76) 0.4939(21) 0.1470(11) 1 3.10(12) H9b H 8 -0.08401(68) 0.5093(20) 0.0188(16) 1 3.10(12) H9c H 8 -0.13321(66) 0.3957(22) 0.0750(14) 1 3.10(12) H2 H 8 0.06638(73) 0.1540(16) 0.0595(14) 1 3.10(12) _vrf_ATOM006_methyl ; PROBLEM: _atom_site_U_iso_or_equiv is missing RESPONSE: Displacement parameters are reported as Biso. The rather high value is due to temperature of data collection of 140 degrees Celsius. ; _vrf_GEOM001_methyl ; PROBLEM: _geom_bond_atom_site_label_1 is missing RESPONSE: Bond lengths and valence angles are not calculated. ; _vrf_GEOM003_methyl ; PROBLEM: _geom_bond_distance is missing RESPONSE: Bond lengths and valence angles are not calculated. ; _vrf_GEOM006_methyl ; PROBLEM: _geom_angle_atom_site_label_2 is missing RESPONSE: Bond lengths and valence angles are not calculated. ; _vrf_GEOM007_methyl ; PROBLEM: _geom_angle_atom_site_label_3 is missing RESPONSE: Bond lengths and valence angles are not calculated. ; _vrf_PLAT761_methyl ; PROBLEM: CIF Contains no X-H Bonds ...................... ? RESPONSE: Bond lengths and valence angles are not calculated. ; _vrf_PLAT762_methyl ; PROBLEM: CIF Contains no X-Y-H or H-Y-H Angles .......... ? RESPONSE: Bond lengths and valence angles are not calculated. ; # end of file