##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
[N,N'-(o-Phenylene)dipicolinamide-κ⁴N]nickel(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H12 N4 Ni O2'
_chemical_formula_sum     'C18 H12 N4 Ni O2  '
_chemical_formula_iupac     '[Ni (C18 H12 N4 O2)]'
_chemical_formula_weight     375.01
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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     7.052(2)
_cell_length_b     18.383(5)
_cell_length_c     11.826(3)
_cell_angle_alpha     90.00
_cell_angle_beta     98.827(4)
_cell_angle_gamma     90.00
_cell_volume     1514.8(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6201
_cell_measurement_theta_min     2.801
_cell_measurement_theta_max     27.854
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.310
_exptl_crystal_size_mid     0.274
_exptl_crystal_size_min     0.215
_exptl_crystal_density_diffrn     1.644
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     768.0
_exptl_absorpt_coefficient_mu     1.301
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 1997)'
_exptl_absorpt_correction_T_min     0.679
_exptl_absorpt_correction_T_max     0.750
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9286
_diffrn_reflns_av_R_equivalents     0.0349
_diffrn_reflns_av_sigmaI/netI     0.0340
_diffrn_reflns_theta_min     2.07
_diffrn_reflns_theta_max     25.49
_diffrn_reflns_theta_full     25.49
_diffrn_measured_fraction_theta_max     0.983
_diffrn_measured_fraction_theta_full     0.983
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -22
_diffrn_reflns_limit_k_max     22
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     <2%
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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     2784
_reflns_number_gt     2087
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0564
_refine_ls_R_factor_gt     0.0446
_refine_ls_wR_factor_gt     0.1148
_refine_ls_wR_factor_ref     0.1191
_refine_ls_goodness_of_fit_ref     1.003
_refine_ls_restrained_S_all     1.214
_refine_ls_number_reflns     2784
_refine_ls_number_parameters     226
_refine_ls_number_restraints     234
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0623P)²+1.4239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.003
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.476
_refine_diff_density_min     -0.563
_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     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 1997)'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Siemens, 1996)'
_computing_publication_material     'SHELXTL (Siemens, 1996)'
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_disorder_assembly
    _atom_site_disorder_group
    Ni Ni1 0.27023(8) 0.49353(2) 0.04659(5) 0.0392(2) Uani d U 1 . .
    N N4 0.3749(5) 0.54985(19) 0.1888(3) 0.0491(5) Uani d U 1 . .
    C C18 0.3852(7) 0.5336(3) 0.2993(4) 0.0525(6) Uani d U 1 . .
    H H18 0.3490 0.4871 0.3189 0.063 Uiso calc R 1 . .
    C C17 0.4466(7) 0.5821(2) 0.3866(4) 0.0557(6) Uani d U 1 . .
    H H17 0.4515 0.5686 0.4627 0.067 Uiso calc R 1 . .
    C C16 0.5004(7) 0.6508(3) 0.3581(4) 0.0562(6) Uani d U 1 . .
    H H16 0.5412 0.6848 0.4148 0.067 Uiso calc R 1 . .
    C C15 0.4931(7) 0.6685(3) 0.2443(4) 0.0537(6) Uani d U 1 . .
    H H15 0.5306 0.7144 0.2234 0.064 Uiso calc R 1 . .
    C C14 0.4297(7) 0.6176(2) 0.1617(4) 0.0496(5) Uani d U 1 . .
    C C13 0.4132(7) 0.6356(2) 0.0369(4) 0.0492(5) Uani d U 1 . .
    C C6 0.2871(7) 0.5805(2) -0.1482(4) 0.0479(5) Uani d U 1 . .
    C C5 0.3207(7) 0.6352(2) -0.2235(4) 0.0513(6) Uani d U 1 . .
    H H5 0.3875 0.6768 -0.1959 0.062 Uiso calc R 1 . .
    C C4 0.2551(7) 0.6281(3) -0.3395(4) 0.0545(6) Uani d U 1 . .
    H H4 0.2796 0.6647 -0.3896 0.065 Uiso calc R 1 . .
    C C3 0.1537(7) 0.5672(3) -0.3814(4) 0.0556(6) Uani d U 1 . .
    H H3 0.1078 0.5636 -0.4592 0.067 Uiso calc R 1 . .
    C C2 0.1194(7) 0.5110(2) -0.3080(4) 0.0530(6) Uani d U 1 . .
    H H2 0.0524 0.4697 -0.3367 0.064 Uiso calc R 1 . .
    C C1 0.1860(7) 0.5172(2) -0.1916(4) 0.0487(5) Uani d U 1 . .
    C C7 0.0884(7) 0.3988(2) -0.1232(4) 0.0508(5) Uani d U 1 . .
    C C8 0.0954(7) 0.3593(2) -0.0110(4) 0.0509(5) Uani d U 1 . .
    C C9 0.0197(7) 0.2900(3) -0.0066(4) 0.0548(6) Uani d U 1 . .
    H H9 -0.0386 0.2672 -0.0731 0.066 Uiso calc R 1 . .
    C C10 0.0318(7) 0.2553(2) 0.0974(4) 0.0570(6) Uani d U 1 . .
    H H10 -0.0191 0.2089 0.1017 0.068 Uiso calc R 1 . .
    C C11 0.1188(7) 0.2894(2) 0.1942(4) 0.0554(6) Uani d U 1 . .
    H H11 0.1289 0.2664 0.2649 0.067 Uiso calc R 1 . .
    C C12 0.1923(7) 0.3591(2) 0.1851(4) 0.0524(6) Uani d U 1 . .
    H H12 0.2520 0.3823 0.2509 0.063 Uiso calc R 1 . .
    N N3 0.1797(5) 0.39376(18) 0.0844(3) 0.0492(5) Uani d U 1 . .
    N N1 0.1611(5) 0.46607(19) -0.1063(3) 0.0477(5) Uani d U 1 . .
    N N2 0.3430(5) 0.57963(18) -0.0291(3) 0.0467(5) Uani d U 1 . .
    O O1 0.0220(5) 0.36873(16) -0.2133(3) 0.0565(6) Uani d U 1 . .
    O O2 0.4605(4) 0.69673(16) 0.0071(3) 0.0542(6) Uani d U 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 0.0475(4) 0.0257(3) 0.0445(3) 0.0000(2) 0.0071(2) -0.0003(2)
    N4 0.0594(12) 0.0381(9) 0.0502(8) -0.0017(9) 0.0098(10) -0.0048(7)
    C18 0.0640(13) 0.0437(11) 0.0501(8) -0.0017(11) 0.0093(12) -0.0053(8)
    C17 0.0667(14) 0.0470(12) 0.0532(10) -0.0011(11) 0.0087(12) -0.0080(9)
    C16 0.0660(14) 0.0458(11) 0.0566(10) -0.0014(11) 0.0085(12) -0.0101(10)
    C15 0.0625(13) 0.0408(10) 0.0578(10) -0.0023(10) 0.0088(12) -0.0086(9)
    C14 0.0584(11) 0.0359(9) 0.0549(8) -0.0023(8) 0.0095(10) -0.0059(7)
    C13 0.0583(11) 0.0329(8) 0.0569(9) -0.0038(8) 0.0101(9) -0.0018(7)
    C6 0.0558(11) 0.0379(9) 0.0507(8) 0.0020(8) 0.0108(9) 0.0026(7)
    C5 0.0587(13) 0.0433(10) 0.0528(10) 0.0032(10) 0.0117(11) 0.0052(9)
    C4 0.0617(13) 0.0495(11) 0.0530(10) 0.0045(10) 0.0113(11) 0.0056(10)
    C3 0.0625(13) 0.0521(12) 0.0525(10) 0.0041(11) 0.0095(11) 0.0028(9)
    C2 0.0598(13) 0.0480(11) 0.0514(9) 0.0028(10) 0.0089(11) -0.0007(9)
    C1 0.0559(11) 0.0408(9) 0.0499(7) 0.0020(8) 0.0095(9) -0.0012(7)
    C7 0.0559(11) 0.0366(9) 0.0601(9) -0.0029(8) 0.0097(9) -0.0076(7)
    C8 0.0544(11) 0.0338(8) 0.0656(10) -0.0025(8) 0.0129(10) -0.0034(7)
    C9 0.0577(13) 0.0363(10) 0.0717(12) -0.0031(9) 0.0139(11) -0.0023(9)
    C10 0.0599(13) 0.0378(11) 0.0748(13) -0.0027(10) 0.0155(12) 0.0026(9)
    C11 0.0595(13) 0.0372(11) 0.0714(12) -0.0016(10) 0.0158(12) 0.0065(9)
    C12 0.0573(13) 0.0353(10) 0.0664(11) -0.0011(10) 0.0151(12) 0.0063(8)
    N3 0.0540(12) 0.0323(9) 0.0629(10) -0.0015(9) 0.0136(11) 0.0020(7)
    N1 0.0549(11) 0.0367(9) 0.0518(8) -0.0018(8) 0.0090(9) -0.0044(7)
    N2 0.0562(11) 0.0325(8) 0.0519(8) -0.0019(8) 0.0098(9) 0.0012(7)
    O1 0.0618(13) 0.0426(11) 0.0642(11) -0.0040(10) 0.0072(11) -0.0110(9)
    O2 0.0641(13) 0.0352(10) 0.0633(12) -0.0068(10) 0.0101(12) -0.0001(9)
_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 . 1.920(4) ?
    Ni1 N2 . 1.926(3) ?
    Ni1 N4 . 2.016(4) ?
    Ni1 N3 . 2.015(3) ?
    N4 C18 . 1.332(6) ?
    N4 C14 . 1.357(5) ?
    C18 C17 . 1.382(6) ?
    C18 H18 . 0.9300 ?
    C17 C16 . 1.374(7) ?
    C17 H17 . 0.9300 ?
    C16 C15 . 1.378(7) ?
    C16 H16 . 0.9300 ?
    C15 C14 . 1.375(6) ?
    C15 H15 . 0.9300 ?
    C14 C13 . 1.500(6) ?
    C13 O2 . 1.238(5) ?
    C13 N2 . 1.339(5) ?
    C6 C5 . 1.388(6) ?
    C6 N2 . 1.403(6) ?
    C6 C1 . 1.419(6) ?
    C5 C4 . 1.386(6) ?
    C5 H5 . 0.9300 ?
    C4 C3 . 1.378(7) ?
    C4 H4 . 0.9300 ?
    C3 C2 . 1.395(6) ?
    C3 H3 . 0.9300 ?
    C2 C1 . 1.389(7) ?
    C2 H2 . 0.9300 ?
    C1 N1 . 1.409(6) ?
    C7 O1 . 1.228(5) ?
    C7 N1 . 1.342(5) ?
    C7 C8 . 1.506(7) ?
    C8 N3 . 1.350(6) ?
    C8 C9 . 1.385(6) ?
    C9 C10 . 1.377(6) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.365(7) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.392(6) ?
    C11 H11 . 0.9300 ?
    C12 N3 . 1.341(6) ?
    C12 H12 . 0.9300 ?
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 N2 . . 82.83(15) ?
    N1 Ni1 N4 . . 164.32(15) ?
    N2 Ni1 N4 . . 82.89(15) ?
    N1 Ni1 N3 . . 82.82(16) ?
    N2 Ni1 N3 . . 165.30(16) ?
    N4 Ni1 N3 . . 111.72(15) ?
    C18 N4 C14 . . 117.6(4) ?
    C18 N4 Ni1 . . 131.4(3) ?
    C14 N4 Ni1 . . 110.8(3) ?
    N4 C18 C17 . . 123.4(5) ?
    N4 C18 H18 . . 118.3 ?
    C17 C18 H18 . . 118.3 ?
    C18 C17 C16 . . 118.5(5) ?
    C18 C17 H17 . . 120.8 ?
    C16 C17 H17 . . 120.8 ?
    C17 C16 C15 . . 119.1(4) ?
    C17 C16 H16 . . 120.5 ?
    C15 C16 H16 . . 120.5 ?
    C14 C15 C16 . . 119.4(4) ?
    C14 C15 H15 . . 120.3 ?
    C16 C15 H15 . . 120.3 ?
    N4 C14 C15 . . 122.0(4) ?
    N4 C14 C13 . . 116.9(4) ?
    C15 C14 C13 . . 121.1(4) ?
    O2 C13 N2 . . 128.5(4) ?
    O2 C13 C14 . . 119.7(4) ?
    N2 C13 C14 . . 111.7(4) ?
    C5 C6 N2 . . 127.0(4) ?
    C5 C6 C1 . . 119.2(4) ?
    N2 C6 C1 . . 113.7(4) ?
    C6 C5 C4 . . 120.2(5) ?
    C6 C5 H5 . . 119.9 ?
    C4 C5 H5 . . 119.9 ?
    C3 C4 C5 . . 120.5(5) ?
    C3 C4 H4 . . 119.7 ?
    C5 C4 H4 . . 119.7 ?
    C4 C3 C2 . . 120.6(5) ?
    C4 C3 H3 . . 119.7 ?
    C2 C3 H3 . . 119.7 ?
    C1 C2 C3 . . 119.4(5) ?
    C1 C2 H2 . . 120.3 ?
    C3 C2 H2 . . 120.3 ?
    C2 C1 N1 . . 126.5(4) ?
    C2 C1 C6 . . 120.0(4) ?
    N1 C1 C6 . . 113.4(4) ?
    O1 C7 N1 . . 129.1(5) ?
    O1 C7 C8 . . 120.3(4) ?
    N1 C7 C8 . . 110.7(4) ?
    N3 C8 C9 . . 121.5(4) ?
    N3 C8 C7 . . 117.5(4) ?
    C9 C8 C7 . . 121.1(4) ?
    C10 C9 C8 . . 119.3(5) ?
    C10 C9 H9 . . 120.4 ?
    C8 C9 H9 . . 120.4 ?
    C11 C10 C9 . . 119.6(4) ?
    C11 C10 H10 . . 120.2 ?
    C9 C10 H10 . . 120.2 ?
    C10 C11 C12 . . 118.9(5) ?
    C10 C11 H11 . . 120.6 ?
    C12 C11 H11 . . 120.6 ?
    N3 C12 C11 . . 122.1(5) ?
    N3 C12 H12 . . 119.0 ?
    C11 C12 H12 . . 119.0 ?
    C12 N3 C8 . . 118.7(4) ?
    C12 N3 Ni1 . . 130.5(3) ?
    C8 N3 Ni1 . . 110.8(3) ?
    C7 N1 C1 . . 126.5(4) ?
    C7 N1 Ni1 . . 118.1(3) ?
    C1 N1 Ni1 . . 115.0(3) ?
    C13 N2 C6 . . 126.7(4) ?
    C13 N2 Ni1 . . 117.5(3) ?
    C6 N2 Ni1 . . 114.9(3) ?
data_global
_journal_date_recd_electronic     2007-08-03
_journal_date_accepted     2007-10-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue     11
_journal_page_first     m2684
_journal_page_last     m2684
_journal_paper_category     QM
_journal_coeditor_code     BV2070
_publ_contact_author_name     'Yin-Qiu Liu '
_publ_contact_author_address
;
      College of Chemistry & Chemical Engineering
      JingGangShan University
      343009 Ji'an, JiangXi
      China
;
_publ_contact_author_email     liuyiqja@163.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     +86-796-13479600226
_publ_section_title
;
[N,N'-(o-Phenylene)dipicolinamide-κ⁴N]nickel(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'Liu, Yin-Qiu'
;
      College of Chemistry & Chemical Engineering
      JiangXi Province Key Laboratory of Coordination Chemistry
      JingGangShan University
      343009 Ji'an, JiangXi
      People's Republic of China
;
    'Zeng, Xi-Rui'
;     College of Chemistry & Chemical Engineering
      JiangXi Province Key Laboratory of Coordination Chemistry
      JingGangShan University
      343009 Ji'an, JiangXi
      People's Republic of China
;
