##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
# 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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Diaquabis(4-methylaminobenzoato-κO)bis(nicotinamide-
κN¹)nickel(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C28 H32 N6 Ni O8'
_chemical_formula_sum     'C28 H32 N6 Ni O8'
_chemical_formula_iupac     '[Ni (C8 H8 N O2)2 (C6 H6 N2 O)2 (H2 O)2]'
_chemical_formula_weight     639.31
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     10.9331(6)
_cell_length_b     9.8467(5)
_cell_length_c     14.1992(8)
_cell_angle_alpha     90.00
_cell_angle_beta     107.4540(10)
_cell_angle_gamma     90.00
_cell_volume     1458.23(14)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     6218
_cell_measurement_theta_min     2.56
_cell_measurement_theta_max     28.36
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.47
_exptl_crystal_size_mid     0.32
_exptl_crystal_size_min     0.31
_exptl_crystal_density_diffrn     1.456
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     668
_exptl_absorpt_coefficient_mu     0.725
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.755
_exptl_absorpt_correction_T_max     0.796
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(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 Kappa APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13201
_diffrn_reflns_av_R_equivalents     0.0275
_diffrn_reflns_av_sigmaI/netI     0.0254
_diffrn_reflns_theta_min     2.08
_diffrn_reflns_theta_max     28.38
_diffrn_reflns_theta_full     28.38
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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     3635
_reflns_number_gt     2954
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0385
_refine_ls_R_factor_gt     0.0299
_refine_ls_wR_factor_gt     0.0807
_refine_ls_wR_factor_ref     0.0847
_refine_ls_goodness_of_fit_ref     1.092
_refine_ls_restrained_S_all     1.115
_refine_ls_number_reflns     3635
_refine_ls_number_parameters     217
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0457P)²+0.1097P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.414
_refine_diff_density_min     -0.424
_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'
    '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'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 0.0000 0.5000 0.0000 0.02520(9) Uani d S 1 . .
    O O1 -0.05431(9) 0.42926(11) 0.11617(7) 0.0298(2) Uani d . 1 . .
    O O2 -0.20986(10) 0.28374(11) 0.03794(7) 0.0331(3) Uani d . 1 . .
    O O3 -0.24476(12) 0.91313(14) -0.21749(8) 0.0441(3) Uani d . 1 . .
    O O4 0.18759(10) 0.52817(12) 0.08904(8) 0.0295(2) Uani d D 1 . .
    H H41 0.209(2) 0.547(2) 0.1523(11) 0.055(6) Uiso d D 1 . .
    H H42 0.212(2) 0.600(2) 0.0608(16) 0.087(9) Uiso d D 1 . .
    N N1 -0.05647(11) 0.69514(13) 0.02746(8) 0.0269(3) Uani d . 1 . .
    N N2 -0.23426(13) 1.10935(16) -0.13262(11) 0.0354(3) Uani d . 1 . .
    H H21 -0.217(2) 1.156(2) -0.0742(16) 0.062(6) Uiso d . 1 . .
    H H22 -0.2690(18) 1.1511(18) -0.1881(14) 0.039(5) Uiso d . 1 . .
    N N3 -0.12888(14) 0.12206(18) 0.48807(10) 0.0422(4) Uani d . 1 . .
    H H31 -0.190(2) 0.071(2) 0.4877(16) 0.061(7) Uiso d . 1 . .
    C C1 -0.13324(13) 0.33378(16) 0.11561(10) 0.0290(3) Uani d . 1 . .
    C C2 -0.13399(13) 0.28004(16) 0.21324(10) 0.0291(3) Uani d . 1 . .
    C C3 -0.21846(14) 0.17675(17) 0.22136(11) 0.0305(3) Uani d . 1 . .
    H H3 -0.2773 0.1428 0.1646 0.037 Uiso calc R 1 . .
    C C4 -0.21573(14) 0.12488(17) 0.31176(11) 0.0328(3) Uani d . 1 . .
    H H4 -0.2723 0.0559 0.3152 0.039 Uiso calc R 1 . .
    C C5 -0.12885(14) 0.17437(18) 0.39904(11) 0.0335(4) Uani d . 1 . .
    C C6 -0.04453(14) 0.27794(18) 0.39144(11) 0.0368(4) Uani d . 1 . .
    H H6 0.0145 0.3121 0.4481 0.044 Uiso calc R 1 . .
    C C7 -0.04892(14) 0.32956(18) 0.29965(11) 0.0334(3) Uani d . 1 . .
    H H7 0.0067 0.3994 0.2959 0.040 Uiso calc R 1 . .
    C C8 -0.04561(13) 0.74589(17) 0.11720(10) 0.0288(3) Uani d . 1 . .
    H H8 -0.0069 0.6930 0.1723 0.035 Uiso calc R 1 . .
    C C9 -0.08955(14) 0.87357(17) 0.13112(11) 0.0321(3) Uani d . 1 . .
    H H9 -0.0814 0.9052 0.1944 0.039 Uiso calc R 1 . .
    C C10 -0.14588(14) 0.95401(18) 0.04957(11) 0.0315(3) Uani d . 1 . .
    H H10 -0.1749 1.0409 0.0571 0.038 Uiso calc R 1 . .
    C C11 -0.15803(13) 0.90173(16) -0.04382(10) 0.0287(3) Uani d . 1 . .
    C C12 -0.11315(13) 0.77289(17) -0.05083(10) 0.0285(3) Uani d . 1 . .
    H H12 -0.1227 0.7378 -0.1134 0.034 Uiso calc R 1 . .
    C C13 -0.21654(14) 0.97680(18) -0.13847(11) 0.0333(4) Uani d . 1 . .
    C C14 -0.04606(17) 0.1690(2) 0.58153(12) 0.0495(5) Uani d . 1 . .
    H H14A -0.0642 0.1195 0.6340 0.074 Uiso calc R 1 . .
    H H14B -0.0605 0.2641 0.5888 0.074 Uiso calc R 1 . .
    H H14C 0.0417 0.1547 0.5841 0.074 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 . 2.0362(9) yes
    Ni1 O1 3_565 2.0362(9) ?
    Ni1 O4 . 2.0800(11) yes
    Ni1 O4 3_565 2.0800(11) ?
    Ni1 N1 . 2.0903(13) yes
    Ni1 N1 3_565 2.0903(13) ?
    O1 C1 . 1.2746(18) ?
    O2 C1 . 1.2675(17) ?
    O3 C13 . 1.2407(19) ?
    O4 H41 . 0.878(14) ?
    O4 H42 . 0.897(16) ?
    N1 C8 . 1.3404(17) ?
    N1 C12 . 1.3389(18) ?
    N2 C13 . 1.326(2) ?
    N2 H21 . 0.92(2) ?
    N2 H22 . 0.869(19) ?
    N3 C14 . 1.440(2) ?
    N3 H31 . 0.83(2) ?
    C2 C1 . 1.4861(19) ?
    C2 C7 . 1.387(2) ?
    C3 C2 . 1.402(2) ?
    C3 C4 . 1.373(2) ?
    C3 H3 . 0.9300 ?
    C4 H4 . 0.9300 ?
    C5 N3 . 1.3652(19) ?
    C5 C4 . 1.403(2) ?
    C5 C6 . 1.400(2) ?
    C6 C7 . 1.386(2) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.381(2) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.386(2) ?
    C9 H9 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C11 C10 . 1.391(2) ?
    C11 C12 . 1.375(2) ?
    C11 C13 . 1.499(2) ?
    C12 H12 . 0.9300 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 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
    O1 Ni1 O1 3_565 . 180.0 ?
    O1 Ni1 O4 . . 91.56(4) ?
    O1 Ni1 O4 3_565 . 88.44(4) ?
    O1 Ni1 O4 3_565 3_565 91.56(4) ?
    O1 Ni1 O4 . 3_565 88.44(4) ?
    O1 Ni1 N1 . . 89.38(4) ?
    O1 Ni1 N1 3_565 . 90.62(4) ?
    O1 Ni1 N1 . 3_565 90.62(4) ?
    O1 Ni1 N1 3_565 3_565 89.38(4) ?
    O4 Ni1 O4 . 3_565 180.00(7) ?
    O4 Ni1 N1 . . 93.24(4) ?
    O4 Ni1 N1 3_565 . 86.76(4) ?
    O4 Ni1 N1 . 3_565 86.76(4) ?
    O4 Ni1 N1 3_565 3_565 93.24(4) ?
    N1 Ni1 N1 3_565 . 180.00(6) ?
    C1 O1 Ni1 . . 127.49(9) ?
    Ni1 O4 H41 . . 123.9(14) ?
    Ni1 O4 H42 . . 102.0(16) ?
    H41 O4 H42 . . 105.4(18) ?
    C8 N1 Ni1 . . 124.97(10) ?
    C12 N1 Ni1 . . 117.37(9) ?
    C12 N1 C8 . . 117.58(13) ?
    C13 N2 H21 . . 123.9(13) ?
    C13 N2 H22 . . 116.2(12) ?
    H21 N2 H22 . . 119.8(18) ?
    C5 N3 C14 . . 123.89(16) ?
    C5 N3 H31 . . 116.4(15) ?
    C14 N3 H31 . . 118.7(15) ?
    O1 C1 C2 . . 116.74(13) ?
    O2 C1 O1 . . 124.17(13) ?
    O2 C1 C2 . . 119.08(13) ?
    C3 C2 C1 . . 121.55(13) ?
    C7 C2 C1 . . 120.67(13) ?
    C7 C2 C3 . . 117.77(13) ?
    C2 C3 H3 . . 119.4 ?
    C4 C3 C2 . . 121.11(14) ?
    C4 C3 H3 . . 119.4 ?
    C3 C4 C5 . . 121.02(15) ?
    C3 C4 H4 . . 119.5 ?
    C5 C4 H4 . . 119.5 ?
    N3 C5 C4 . . 119.91(15) ?
    N3 C5 C6 . . 121.94(15) ?
    C6 C5 C4 . . 118.14(13) ?
    C5 C6 H6 . . 120.0 ?
    C7 C6 C5 . . 120.10(14) ?
    C7 C6 H6 . . 120.0 ?
    C2 C7 H7 . . 119.1 ?
    C6 C7 C2 . . 121.85(15) ?
    C6 C7 H7 . . 119.1 ?
    N1 C8 C9 . . 122.69(13) ?
    N1 C8 H8 . . 118.7 ?
    C9 C8 H8 . . 118.7 ?
    C8 C9 C10 . . 119.16(14) ?
    C8 C9 H9 . . 120.4 ?
    C10 C9 H9 . . 120.4 ?
    C9 C10 C11 . . 118.46(15) ?
    C9 C10 H10 . . 120.8 ?
    C11 C10 H10 . . 120.8 ?
    C10 C11 C13 . . 124.42(15) ?
    C12 C11 C10 . . 118.45(13) ?
    C12 C11 C13 . . 117.12(13) ?
    N1 C12 C11 . . 123.64(13) ?
    N1 C12 H12 . . 118.2 ?
    C11 C12 H12 . . 118.2 ?
    O3 C13 N2 . . 123.55(15) ?
    O3 C13 C11 . . 119.03(15) ?
    N2 C13 C11 . . 117.41(14) ?
    N3 C14 H14A . . 109.5 ?
    N3 C14 H14B . . 109.5 ?
    N3 C14 H14C . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 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
    O4 Ni1 O1 C1 . . . . -142.35(12) ?
    O4 Ni1 O1 C1 3_565 . . . 37.65(12) ?
    N1 Ni1 O1 C1 3_565 . . . -55.58(12) ?
    N1 Ni1 O1 C1 . . . . 124.42(12) ?
    O1 Ni1 N1 C8 3_565 . . . -145.11(11) ?
    O1 Ni1 N1 C8 . . . . 34.89(11) ?
    O1 Ni1 N1 C12 3_565 . . . 38.14(10) ?
    O1 Ni1 N1 C12 . . . . -141.86(10) ?
    O4 Ni1 N1 C8 . . . . -56.63(11) ?
    O4 Ni1 N1 C8 3_565 . . . 123.37(11) ?
    O4 Ni1 N1 C12 . . . . 126.62(10) ?
    O4 Ni1 N1 C12 3_565 . . . -53.38(10) ?
    Ni1 O1 C1 O2 . . . . -14.1(2) ?
    Ni1 O1 C1 C2 . . . . 166.19(9) ?
    Ni1 N1 C8 C9 . . . . -177.10(11) ?
    C12 N1 C8 C9 . . . . -0.4(2) ?
    Ni1 N1 C12 C11 . . . . 178.29(11) ?
    C8 N1 C12 C11 . . . . 1.3(2) ?
    C3 C2 C1 O1 . . . . 178.85(13) ?
    C3 C2 C1 O2 . . . . -0.8(2) ?
    C7 C2 C1 O1 . . . . -2.2(2) ?
    C7 C2 C1 O2 . . . . 178.09(14) ?
    C1 C2 C7 C6 . . . . -177.70(14) ?
    C3 C2 C7 C6 . . . . 1.3(2) ?
    C4 C3 C2 C1 . . . . 177.98(14) ?
    C4 C3 C2 C7 . . . . -1.0(2) ?
    C2 C3 C4 C5 . . . . 0.5(2) ?
    C4 C5 N3 C14 . . . . -178.12(16) ?
    C6 C5 N3 C14 . . . . 1.4(3) ?
    N3 C5 C4 C3 . . . . 179.35(15) ?
    N3 C5 C6 C7 . . . . -179.07(16) ?
    C4 C5 C6 C7 . . . . 0.5(2) ?
    C6 C5 C4 C3 . . . . -0.2(2) ?
    C5 C6 C7 C2 . . . . -1.1(3) ?
    N1 C8 C9 C10 . . . . -0.8(2) ?
    C8 C9 C10 C11 . . . . 1.1(2) ?
    C12 C11 C10 C9 . . . . -0.2(2) ?
    C13 C11 C10 C9 . . . . -179.89(14) ?
    C10 C11 C12 N1 . . . . -1.0(2) ?
    C13 C11 C12 N1 . . . . 178.68(13) ?
    C10 C11 C13 O3 . . . . -166.51(15) ?
    C10 C11 C13 N2 . . . . 14.0(2) ?
    C12 C11 C13 O3 . . . . 13.8(2) ?
    C12 C11 C13 N2 . . . . -165.61(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
    N2 H21 O2 1_565 0.92(2) 2.01(2) 2.9150(18) 167.9(18) yes
    N3 H31 O4 4_566 0.84(2) 2.44(2) 3.162(2) 144.6(19) yes
    O4 H41 O3 4_676 0.877(15) 1.808(15) 2.6849(16) 179(2) yes
    O4 H42 O2 3_565 0.89(2) 1.80(2) 2.6464(15) 156(2) yes
data_global
_journal_date_recd_electronic     2009-04-24
_journal_date_accepted     2009-04-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      5
_journal_page_first     m605
_journal_page_last     m606
_journal_paper_category     QM
_journal_coeditor_code     XU2516
_publ_contact_author
;
Dr. Tuncer Hökelek
Hacettepe University
Department of Physics
06800 Beytepe
Ankara
Turkey
;
_publ_contact_author_email     merzifon@hacettepe.edu.tr
_publ_contact_author_fax     '90(312)2352550'
_publ_contact_author_phone     '90(312)2977242'
_publ_section_title
;\
Diaquabis(4-methylaminobenzoato-κO)bis(nicotinamide-κN¹)\
nickel(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'Hökelek, Tuncer'
;
Department of Physics
Hacettepe University
06800 Beytepe
Ankara
Turkey
;
    'Dal, Hakan'
;
Department of Chemistry
Faculty of Science
Anadolu University
26470 Yenibağlar
Eskişehir
Turkey
;
    'Tercan, Barış'
;
Department of Physics
Karabük University
78050 Karabük
Turkey
;
    'Aybirdi, Özgür'
;
Department of Chemistry
Kafkas University
63100 Kars
Turkey
;
    'Necefoğlu, Hacali'
;
Department of Chemistry
Kafkas University
63100 Kars
Turkey
;
