############################################################################## # # # This CIF contains the data in a paper accepted for publication in # # Acta Crystallographica Section E. It conforms to the requirements of # # Notes for Authors for Acta Crystallographica Section E, and has been # # peer reviewed under the auspices of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. # # # # Software is freely available for graphical display of the structure(s) # # in this CIF. For information consult the CIF software page # # http://www.iucr.org/resources/cif/software. # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_global _audit_creation_method 'form.cif (version 2.0)' _journal_data_validation_number ? _journal_date_recd_electronic 2013-05-05 _journal_date_accepted 2013-05-09 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2013 _journal_volume 69 _journal_issue 6 _journal_page_first m322 _journal_page_last m322 _journal_paper_category QM _journal_paper_doi 10.1107/S1600536813012816 _journal_coeditor_code SU2598 _publ_contact_author_name 'Gurbanov, Atash V.' _publ_contact_author_address ; Department of Organic Chemistry, Baku State University, Baku, Azerbaijan ; _publ_contact_author_email 'organik10@hotmail.com' _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_section_title ; [Hexane-2,5-dione bis(thiosemicarbazonato)]nickel(II) ; loop_ _publ_author_name _publ_author_address 'Shalamzari, Mohammad Safi' ; Department of Pharmaceutical Sciences, University of Antwerp, Antwerp, Belgium ; 'Gurbanov, Atash V.' ; Department of Organic Chemistry, Baku State University, Baku, Azerbaijan ; 'Heidic, Seykens' ; Department of Chemistry, University of Antwerp, Antwerp, Belgium ; 'Kia, Reza' ; Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran Deutsches Elektronen-Synchrotron (DESY), Division Structural Dynamics of (Bio)chemical Systems, Notkestrasse 85, 22607 Hamburg, Germany ; 'Behrouzi, Shabnam' ; Department of Pharmaceutical Sciences, University of Antwerp, Antwerp, Belgium ; data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; [Hexane-2,5-dione bis(thiosemicarbazonato)]nickel(II) ; _chemical_name_common ? _chemical_formula_moiety 'C8 H14 N6 Ni S2' _chemical_formula_sum 'C8 H14 N6 Ni S2' _chemical_formula_iupac '[Ni (C8 H14 N6 S2)]' _chemical_formula_weight 317.08 _chemical_melting_point_lt 468 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8928(3) _cell_length_b 8.0378(3) _cell_length_c 11.0889(4) _cell_angle_alpha 69.7200(10) _cell_angle_beta 75.2140(10) _cell_angle_gamma 85.6930(10) _cell_volume 637.96(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4799 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 28.32 _cell_measurement_temperature 296(2) _exptl_crystal_description prism _exptl_crystal_colour 'dark-red' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 1.835 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2005)' _exptl_absorpt_correction_T_min 0.7105 _exptl_absorpt_correction_T_max 0.7105 _exptl_special_details ? _diffrn_ambient_temperature 296(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7275 _diffrn_reflns_av_R_equivalents 0.0109 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _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. ; _reflns_number_total 3078 _reflns_number_gt 2833 _reflns_threshold_expression 'I>2\s(I)' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0231 _refine_ls_R_factor_gt 0.0209 _refine_ls_wR_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.0587 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _refine_ls_number_reflns 3078 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+0.1248P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.277 _refine_diff_density_min -0.210 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' 'S' 'S' 0.1246 0.1234 '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' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2005)' _computing_data_reduction 'SAINT-Plus (Bruker, 2005)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni1 0.74078(2) 0.65209(2) 0.792634(16) 0.02818(7) Uani d . 1 1 . . S S1 0.67960(5) 0.84581(4) 0.61696(4) 0.03729(9) Uani d . 1 1 . . S S2 0.69288(5) 0.85168(4) 0.88575(4) 0.03624(9) Uani d . 1 1 . . N N1 0.77048(15) 0.49799(14) 0.69038(11) 0.0297(2) Uani d . 1 1 . . N N2 0.65361(17) 0.51991(15) 0.60798(12) 0.0336(2) Uani d . 1 1 . . N N3 0.5029(2) 0.73756(19) 0.48368(16) 0.0567(4) Uani d . 1 1 . . H H1N3 0.4658 0.8503 0.4602 0.068 Uiso d R 1 1 . . H H2N3 0.4647 0.6561 0.4575 0.068 Uiso d R 1 1 . . N N4 0.75863(15) 0.48253(15) 0.96705(12) 0.0314(2) Uani d . 1 1 . . N N5 0.66994(18) 0.53312(16) 1.07736(12) 0.0381(3) Uani d . 1 1 . . N N6 0.57514(19) 0.76724(18) 1.14636(13) 0.0432(3) Uani d . 1 1 . . H H1N6 0.5353 0.6876 1.2274 0.052 Uiso d R 1 1 . . H H2N6 0.5298 0.8801 1.1246 0.052 Uiso d R 1 1 . . C C1 0.6069(2) 0.68543(18) 0.56807(14) 0.0350(3) Uani d . 1 1 . . C C2 0.64152(18) 0.70094(18) 1.04654(14) 0.0321(3) Uani d . 1 1 . . C C3 0.8992(2) 0.2587(2) 0.60870(16) 0.0427(3) Uani d . 1 1 . . H H3A 0.8689 0.3227 0.5264 0.064 Uiso calc R 1 1 . . H H3B 0.8197 0.1599 0.6581 0.064 Uiso calc R 1 1 . . H H3C 1.0167 0.2163 0.5910 0.064 Uiso calc R 1 1 . . C C4 0.88697(18) 0.37854(18) 0.68727(14) 0.0321(3) Uani d . 1 1 . . C C5 1.01427(19) 0.3582(2) 0.77028(16) 0.0389(3) Uani d . 1 1 . . H H5A 1.0445 0.4742 0.7680 0.047 Uiso calc R 1 1 . . H H5B 1.1207 0.3055 0.7337 0.047 Uiso calc R 1 1 . . C C6 0.9390(2) 0.24249(19) 0.91302(16) 0.0376(3) Uani d . 1 1 . . H H6A 0.8753 0.1449 0.9115 0.045 Uiso calc R 1 1 . . H H6B 1.0366 0.1917 0.9514 0.045 Uiso calc R 1 1 . . C C7 0.82010(18) 0.32434(18) 1.00507(15) 0.0336(3) Uani d . 1 1 . . C C8 0.7864(2) 0.2088(2) 1.14834(17) 0.0457(4) Uani d . 1 1 . . H H8A 0.6655 0.2164 1.1913 0.069 Uiso calc R 1 1 . . H H8B 0.8593 0.2480 1.1909 0.069 Uiso calc R 1 1 . . H H8C 0.8131 0.0881 1.1543 0.069 Uiso calc R 1 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Ni1 0.03387(10) 0.02086(9) 0.03506(10) 0.00579(6) -0.01551(7) -0.01199(7) S1 0.0556(2) 0.02174(16) 0.04102(19) 0.00748(14) -0.02323(16) -0.01184(14) S2 0.0531(2) 0.02249(16) 0.03655(18) 0.00501(14) -0.01499(15) -0.01232(13) N1 0.0350(6) 0.0238(5) 0.0344(6) 0.0044(4) -0.0139(4) -0.0118(4) N2 0.0452(6) 0.0261(5) 0.0369(6) 0.0078(5) -0.0209(5) -0.0136(5) N3 0.0945(12) 0.0322(7) 0.0674(9) 0.0223(7) -0.0587(9) -0.0231(7) N4 0.0343(6) 0.0259(5) 0.0382(6) 0.0036(4) -0.0154(5) -0.0119(5) N5 0.0465(7) 0.0305(6) 0.0376(6) 0.0068(5) -0.0131(5) -0.0111(5) N6 0.0557(8) 0.0364(7) 0.0375(7) 0.0089(6) -0.0092(6) -0.0156(5) C1 0.0487(8) 0.0267(6) 0.0352(7) 0.0080(6) -0.0181(6) -0.0132(5) C2 0.0335(6) 0.0296(6) 0.0371(7) 0.0023(5) -0.0138(5) -0.0129(5) C3 0.0498(9) 0.0348(7) 0.0471(8) 0.0102(6) -0.0098(7) -0.0219(7) C4 0.0337(6) 0.0249(6) 0.0372(7) 0.0026(5) -0.0084(5) -0.0106(5) C5 0.0307(6) 0.0355(7) 0.0549(9) 0.0079(5) -0.0151(6) -0.0190(7) C6 0.0402(7) 0.0279(7) 0.0519(8) 0.0116(6) -0.0239(6) -0.0158(6) C7 0.0341(6) 0.0259(6) 0.0448(7) 0.0034(5) -0.0200(6) -0.0105(6) C8 0.0503(9) 0.0325(7) 0.0487(9) 0.0077(6) -0.0185(7) -0.0038(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ni1 N1 . 1.9155(11) ? Ni1 N4 . 1.9751(12) ? Ni1 S2 . 2.1542(4) ? Ni1 S1 . 2.1718(4) ? S1 C1 . 1.7434(14) ? S2 C2 . 1.7374(15) ? N1 C4 . 1.2816(18) ? N1 N2 . 1.4181(15) ? N2 C1 . 1.3051(17) ? N3 C1 . 1.3392(19) ? N3 H1N3 . 0.9003 ? N3 H2N3 . 0.9003 ? N4 C7 . 1.2923(17) ? N4 N5 . 1.4202(17) ? N5 C2 . 1.2887(18) ? N6 C2 . 1.3619(18) ? N6 H1N6 . 0.8959 ? N6 H2N6 . 0.9237 ? C3 C4 . 1.490(2) ? C3 H3A . 0.9600 ? C3 H3B . 0.9600 ? C3 H3C . 0.9600 ? C4 C5 . 1.4922(19) ? C5 C6 . 1.518(2) ? C5 H5A . 0.9700 ? C5 H5B . 0.9700 ? C6 C7 . 1.496(2) ? C6 H6A . 0.9700 ? C6 H6B . 0.9700 ? C7 C8 . 1.502(2) ? C8 H8A . 0.9600 ? C8 H8B . 0.9600 ? C8 H8C . 0.9600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 Ni1 N4 . . 101.11(5) ? N1 Ni1 S2 . . 171.94(3) ? N4 Ni1 S2 . . 86.61(3) ? N1 Ni1 S1 . . 83.28(3) ? N4 Ni1 S1 . . 170.95(4) ? S2 Ni1 S1 . . 88.755(14) ? C1 S1 Ni1 . . 93.57(5) ? C2 S2 Ni1 . . 94.83(5) ? C4 N1 N2 . . 116.52(11) ? C4 N1 Ni1 . . 126.65(10) ? N2 N1 Ni1 . . 116.82(8) ? C1 N2 N1 . . 109.69(11) ? C1 N3 H1N3 . . 119.4 ? C1 N3 H2N3 . . 118.7 ? H1N3 N3 H2N3 . . 121.7 ? C7 N4 N5 . . 111.17(12) ? C7 N4 Ni1 . . 133.49(10) ? N5 N4 Ni1 . . 114.93(8) ? C2 N5 N4 . . 113.32(12) ? C2 N6 H1N6 . . 116.4 ? C2 N6 H2N6 . . 117.9 ? H1N6 N6 H2N6 . . 120.2 ? N2 C1 N3 . . 119.68(13) ? N2 C1 S1 . . 122.47(11) ? N3 C1 S1 . . 117.82(11) ? N5 C2 N6 . . 118.33(13) ? N5 C2 S2 . . 124.34(11) ? N6 C2 S2 . . 117.25(11) ? C4 C3 H3A . . 109.5 ? C4 C3 H3B . . 109.5 ? H3A C3 H3B . . 109.5 ? C4 C3 H3C . . 109.5 ? H3A C3 H3C . . 109.5 ? H3B C3 H3C . . 109.5 ? N1 C4 C5 . . 117.00(12) ? N1 C4 C3 . . 123.93(13) ? C5 C4 C3 . . 119.06(13) ? C4 C5 C6 . . 111.47(12) ? C4 C5 H5A . . 109.3 ? C6 C5 H5A . . 109.3 ? C4 C5 H5B . . 109.3 ? C6 C5 H5B . . 109.3 ? H5A C5 H5B . . 108.0 ? C7 C6 C5 . . 118.83(12) ? C7 C6 H6A . . 107.6 ? C5 C6 H6A . . 107.6 ? C7 C6 H6B . . 107.6 ? C5 C6 H6B . . 107.6 ? H6A C6 H6B . . 107.0 ? N4 C7 C8 . . 122.59(14) ? N4 C7 C6 . . 123.82(13) ? C8 C7 C6 . . 113.50(12) ? C7 C8 H8A . . 109.5 ? C7 C8 H8B . . 109.5 ? H8A C8 H8B . . 109.5 ? C7 C8 H8C . . 109.5 ? H8A C8 H8C . . 109.5 ? H8B C8 H8C . . 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N1 Ni1 S1 C1 . . . . 26.73(7) ? S2 Ni1 S1 C1 . . . . -152.05(6) ? N4 Ni1 S2 C2 . . . . -17.03(6) ? S1 Ni1 S2 C2 . . . . 155.19(5) ? N4 Ni1 N1 C4 . . . . -46.03(13) ? S1 Ni1 N1 C4 . . . . 141.98(12) ? N4 Ni1 N1 N2 . . . . 135.05(9) ? S1 Ni1 N1 N2 . . . . -36.94(9) ? C4 N1 N2 C1 . . . . -148.40(13) ? Ni1 N1 N2 C1 . . . . 30.63(15) ? N1 Ni1 N4 C7 . . . . 18.12(14) ? S2 Ni1 N4 C7 . . . . -164.20(13) ? N1 Ni1 N4 N5 . . . . -153.75(9) ? S2 Ni1 N4 N5 . . . . 23.93(9) ? C7 N4 N5 C2 . . . . 165.09(13) ? Ni1 N4 N5 C2 . . . . -21.23(15) ? N1 N2 C1 N3 . . . . 176.82(15) ? N1 N2 C1 S1 . . . . -1.41(18) ? Ni1 S1 C1 N2 . . . . -21.81(14) ? Ni1 S1 C1 N3 . . . . 159.93(14) ? N4 N5 C2 N6 . . . . -172.75(12) ? N4 N5 C2 S2 . . . . 3.74(18) ? Ni1 S2 C2 N5 . . . . 12.62(13) ? Ni1 S2 C2 N6 . . . . -170.86(11) ? N2 N1 C4 C5 . . . . 178.11(12) ? Ni1 N1 C4 C5 . . . . -0.80(19) ? N2 N1 C4 C3 . . . . -3.2(2) ? Ni1 N1 C4 C3 . . . . 177.87(11) ? N1 C4 C5 C6 . . . . 83.18(16) ? C3 C4 C5 C6 . . . . -95.57(16) ? C4 C5 C6 C7 . . . . -82.08(16) ? N5 N4 C7 C8 . . . . 4.41(19) ? Ni1 N4 C7 C8 . . . . -167.68(11) ? N5 N4 C7 C6 . . . . -171.94(13) ? Ni1 N4 C7 C6 . . . . 16.0(2) ? C5 C6 C7 N4 . . . . 9.3(2) ? C5 C6 C7 C8 . . . . -167.36(13) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N3 H2N3 N2 2_666 0.90 2.16 3.054(2) 173 yes N3 H1N3 S1 2_676 0.90 2.58 3.4699(17) 171 yes N6 H1N6 N2 2_667 0.90 2.28 3.1248(19) 156 yes N6 H2N6 S2 2_677 0.92 2.67 3.5552(16) 162 yes C3 H3B S2 1_545 0.96 2.87 3.7513(17) 152 yes