############################################################################## # # # 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 2011-12-11 _journal_date_accepted 2011-12-16 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2012 _journal_volume 68 _journal_issue 1 _journal_page_first m82 _journal_page_last m82 _journal_paper_category QM _journal_paper_doi 10.1107/S1600536811054262 _journal_coeditor_code LH5396 _publ_contact_author_name 'Prof. Tahir, Muhammad Nawaz' _publ_contact_author_address ; Department of Physics University of Sargodha Punjab Pakistan ; _publ_contact_author_email dmntahir_uos@yahoo.com _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_section_title ;\ {4,4'-Dimethyl-2,2'-[(2,2-dimethylpropane-1,3-diyl)bis(nitrilomethanylylidene)]\ diphenolato}nickel(II) monohydrate ; loop_ _publ_author_name _publ_author_address 'Kargar, Hadi' ; Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran ; 'Kia, Reza' ; X-ray Crystallography Lab., Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran and Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran ; 'Sharafi, Zahra' ; Department of Chemistry, Marvdasht Branch, Islamic Azad University, Marvdasht, Iran ; 'Tahir, Muhammad Nawaz' ; Department of Physics University of Sargodha Punjab, Pakistan ; data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; {4,4'-Dimethyl-2,2'-[(2,2-dimethylpropane-1,3- diyl)bis(nitrilomethanylylidene)]diphenolato}nickel(II) monohydrate ; _chemical_name_common ; ; _chemical_formula_moiety 'C21 H24 N2 Ni O2, H2 O' _chemical_formula_sum 'C21 H26 N2 Ni O3' _chemical_formula_iupac '[Ni (C21 H24 N2 O2)], H2 O' _chemical_formula_weight 413.15 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 13.3333(4) _cell_length_b 15.9424(5) _cell_length_c 9.9965(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.7360(10) _cell_angle_gamma 90.00 _cell_volume 2055.01(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3245 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 27.80 _cell_measurement_temperature 296(2) _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.966 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2005)' _exptl_absorpt_correction_T_min 0.7942 _exptl_absorpt_correction_T_max 0.9267 _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 SMART APEXII CCD area-detector ; _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17468 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 28.31 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _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 2557 _reflns_number_gt 2131 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.0827 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_number_reflns 2557 _refine_ls_number_parameters 125 _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^)+(0.0485P)^2^] 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 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.206 _refine_diff_density_min -0.309 _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' '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' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' 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 0.0000 0.489837(15) 0.2500 0.03589(11) Uani d S 1 2 . . O O1 0.09186(9) 0.57316(6) 0.34800(11) 0.0457(3) Uani d . 1 1 . . N N1 0.04523(10) 0.40475(8) 0.39178(12) 0.0414(3) Uani d . 1 1 . . C C1 0.16634(12) 0.56212(9) 0.46203(15) 0.0401(3) Uani d . 1 1 . . C C2 0.23779(14) 0.62692(10) 0.50786(17) 0.0497(4) Uani d . 1 1 . . H H2A 0.2346 0.6747 0.4537 0.060 Uiso calc R 1 1 . . C C3 0.31279(14) 0.62162(12) 0.63132(18) 0.0567(5) Uani d . 1 1 . . H H3A 0.3589 0.6660 0.6581 0.068 Uiso calc R 1 1 . . C C4 0.32147(14) 0.55163(13) 0.71719(17) 0.0550(4) Uani d . 1 1 . . C C5 0.25490(14) 0.48675(11) 0.67168(18) 0.0487(4) Uani d . 1 1 . . H H5A 0.2604 0.4390 0.7265 0.058 Uiso calc R 1 1 . . C C6 0.17758(13) 0.48878(9) 0.54427(17) 0.0410(3) Uani d . 1 1 . . C C7 0.40114(17) 0.54821(18) 0.85526(19) 0.0817(7) Uani d . 1 1 . . H H7A 0.4556 0.5101 0.8494 0.123 Uiso calc R 1 1 . . H H7B 0.3687 0.5292 0.9252 0.123 Uiso calc R 1 1 . . H H7C 0.4297 0.6031 0.8788 0.123 Uiso calc R 1 1 . . C C8 0.11388(13) 0.41566(10) 0.50691(15) 0.0431(4) Uani d . 1 1 . . H H8A 0.1230 0.3725 0.5714 0.052 Uiso calc R 1 1 . . C C9 -0.01669(14) 0.32780(10) 0.36982(16) 0.0488(4) Uani d . 1 1 . . H H9A -0.0895 0.3426 0.3512 0.059 Uiso calc R 1 1 . . H H9B 0.0006 0.2949 0.4542 0.059 Uiso calc R 1 1 . . C C10 0.0000 0.27358(15) 0.2500 0.0564(7) Uani d S 1 2 . . C C11 0.0973(2) 0.21930(15) 0.2981(2) 0.1038(9) Uani d . 1 1 . . H H11A 0.1569 0.2548 0.3287 0.156 Uiso calc R 1 1 . . H H11B 0.1057 0.1851 0.2226 0.156 Uiso calc R 1 1 . . H H11C 0.0903 0.1840 0.3729 0.156 Uiso calc R 1 1 . . O O1W 0.0000 0.72531(12) 0.2500 0.0992(8) Uani d S 1 2 . . H H1 -0.0556 0.6878 0.2007 0.149 Uiso d 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 0.03715(18) 0.03024(16) 0.03666(16) 0.000 0.00274(11) 0.000 O1 0.0462(7) 0.0353(6) 0.0472(6) -0.0002(5) -0.0032(5) 0.0020(5) N1 0.0448(8) 0.0367(7) 0.0424(7) -0.0023(6) 0.0110(6) 0.0012(5) C1 0.0364(8) 0.0408(8) 0.0418(8) 0.0035(6) 0.0075(6) -0.0040(6) C2 0.0470(10) 0.0449(9) 0.0540(9) -0.0035(7) 0.0069(8) -0.0022(7) C3 0.0434(10) 0.0635(12) 0.0586(10) -0.0101(8) 0.0047(8) -0.0118(9) C4 0.0391(10) 0.0794(13) 0.0432(9) -0.0003(9) 0.0042(7) -0.0047(9) C5 0.0428(10) 0.0604(11) 0.0413(8) 0.0055(8) 0.0076(7) 0.0051(7) C6 0.0373(9) 0.0449(9) 0.0390(8) 0.0040(7) 0.0065(7) -0.0010(6) C7 0.0590(14) 0.121(2) 0.0537(11) -0.0122(13) -0.0074(10) -0.0005(12) C8 0.0472(10) 0.0411(8) 0.0408(8) 0.0029(7) 0.0109(7) 0.0055(6) C9 0.0603(11) 0.0394(9) 0.0494(9) -0.0103(8) 0.0189(8) 0.0006(7) C10 0.0806(19) 0.0355(12) 0.0563(14) 0.000 0.0236(14) 0.000 C11 0.159(3) 0.0726(15) 0.0929(16) 0.0629(16) 0.0553(17) 0.0332(13) O1W 0.1069(18) 0.0426(11) 0.1201(18) 0.000 -0.0225(15) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ni1 O1 . 1.9010(10) n Ni1 O1 2 1.9010(10) . Ni1 N1 2 1.9436(12) n Ni1 N1 . 1.9436(12) ? O1 C1 . 1.3194(17) ? N1 C8 . 1.2870(19) ? N1 C9 . 1.4638(19) ? C1 C2 . 1.401(2) ? C1 C6 . 1.415(2) ? C2 C3 . 1.379(2) ? C2 H2A . 0.9300 ? C3 C4 . 1.394(3) ? C3 H3A . 0.9300 ? C4 C5 . 1.364(3) ? C4 C7 . 1.513(2) ? C5 C6 . 1.421(2) ? C5 H5A . 0.9300 ? C6 C8 . 1.435(2) ? C7 H7A . 0.9600 ? C7 H7B . 0.9600 ? C7 H7C . 0.9600 ? C8 H8A . 0.9300 ? C9 C10 . 1.539(2) ? C9 H9A . 0.9700 ? C9 H9B . 0.9700 ? C10 C11 . 1.532(2) ? C10 C11 2 1.532(2) ? C10 C9 2 1.539(2) ? C11 H11A . 0.9600 ? C11 H11B . 0.9600 ? C11 H11C . 0.9600 ? O1W H1 . 0.9818 ? 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 O1 Ni1 O1 . 2 91.34(6) n O1 Ni1 N1 . 2 154.58(6) n O1 Ni1 N1 2 2 94.14(5) n O1 Ni1 N1 . . 94.14(5) ? O1 Ni1 N1 2 . 154.58(6) ? N1 Ni1 N1 2 . 91.48(7) n C1 O1 Ni1 . . 126.63(9) ? C8 N1 C9 . . 119.54(13) ? C8 N1 Ni1 . . 125.16(11) ? C9 N1 Ni1 . . 114.64(10) ? O1 C1 C2 . . 118.94(14) ? O1 C1 C6 . . 123.87(14) ? C2 C1 C6 . . 117.16(15) ? C3 C2 C1 . . 121.69(16) ? C3 C2 H2A . . 119.2 ? C1 C2 H2A . . 119.2 ? C2 C3 C4 . . 121.84(17) ? C2 C3 H3A . . 119.1 ? C4 C3 H3A . . 119.1 ? C5 C4 C3 . . 117.16(16) ? C5 C4 C7 . . 121.55(19) ? C3 C4 C7 . . 121.28(19) ? C4 C5 C6 . . 122.98(17) ? C4 C5 H5A . . 118.5 ? C6 C5 H5A . . 118.5 ? C1 C6 C5 . . 119.02(15) ? C1 C6 C8 . . 123.49(15) ? C5 C6 C8 . . 117.48(14) ? C4 C7 H7A . . 109.5 ? C4 C7 H7B . . 109.5 ? H7A C7 H7B . . 109.5 ? C4 C7 H7C . . 109.5 ? H7A C7 H7C . . 109.5 ? H7B C7 H7C . . 109.5 ? N1 C8 C6 . . 125.58(15) ? N1 C8 H8A . . 117.2 ? C6 C8 H8A . . 117.2 ? N1 C9 C10 . . 113.57(13) ? N1 C9 H9A . . 108.9 ? C10 C9 H9A . . 108.9 ? N1 C9 H9B . . 108.9 ? C10 C9 H9B . . 108.9 ? H9A C9 H9B . . 107.7 ? C11 C10 C11 . 2 111.2(3) ? C11 C10 C9 . 2 106.43(11) ? C11 C10 C9 2 2 110.61(11) ? C11 C10 C9 . . 110.61(11) ? C11 C10 C9 2 . 106.43(11) ? C9 C10 C9 2 . 111.63(18) ? C10 C11 H11A . . 109.5 ? C10 C11 H11B . . 109.5 ? H11A C11 H11B . . 109.5 ? C10 C11 H11C . . 109.5 ? H11A C11 H11C . . 109.5 ? H11B C11 H11C . . 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 O1 Ni1 O1 C1 2 . . . 163.48(15) ? N1 Ni1 O1 C1 2 . . . -93.95(16) ? N1 Ni1 O1 C1 . . . . 8.32(13) ? O1 Ni1 N1 C8 . . . . 1.34(13) ? O1 Ni1 N1 C8 2 . . . -100.61(16) ? N1 Ni1 N1 C8 2 . . . 156.53(16) ? O1 Ni1 N1 C9 . . . . 171.99(11) ? O1 Ni1 N1 C9 2 . . . 70.04(15) ? N1 Ni1 N1 C9 2 . . . -32.82(8) ? Ni1 O1 C1 C2 . . . . 169.47(11) ? Ni1 O1 C1 C6 . . . . -12.1(2) ? O1 C1 C2 C3 . . . . 175.28(15) ? C6 C1 C2 C3 . . . . -3.2(2) ? C1 C2 C3 C4 . . . . -0.1(3) ? C2 C3 C4 C5 . . . . 2.4(3) ? C2 C3 C4 C7 . . . . -177.33(18) ? C3 C4 C5 C6 . . . . -1.3(3) ? C7 C4 C5 C6 . . . . 178.41(17) ? O1 C1 C6 C5 . . . . -174.24(15) ? C2 C1 C6 C5 . . . . 4.2(2) ? O1 C1 C6 C8 . . . . 5.0(2) ? C2 C1 C6 C8 . . . . -176.58(15) ? C4 C5 C6 C1 . . . . -2.0(3) ? C4 C5 C6 C8 . . . . 178.70(16) ? C9 N1 C8 C6 . . . . -177.90(15) ? Ni1 N1 C8 C6 . . . . -7.7(2) ? C1 C6 C8 N1 . . . . 5.6(3) ? C5 C6 C8 N1 . . . . -175.14(16) ? C8 N1 C9 C10 . . . . -117.17(16) ? Ni1 N1 C9 C10 . . . . 71.61(15) ? N1 C9 C10 C11 . . . . 82.3(2) ? N1 C9 C10 C11 . . . 2 -156.78(16) ? N1 C9 C10 C9 . . . 2 -36.00(9) ? 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 O1W H1 O1 2_555 0.98 1.92 2.781(2) 145 y C3 H3A O1W 7_566 0.93 2.55 3.477(2) 173 y