#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/25/2222509.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222509
loop_
_publ_author_name
'Hökelek, Tuncer'
'Yılmaz, Filiz'
'Tercan, Barış'
'Özbek, F. Elif'
'Necefoğlu, Hacali'
_publ_section_title
Diaquabis(2-bromobenzoato-κO)bis(nicotinamide-κN¹)nickel(II)
_journal_coeditor_code           XU2538
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m768
_journal_page_last               m769
_journal_paper_doi               10.1107/S1600536809021710
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Ni (C7 H4 Br O2)2 (C6 H6 N2 O)2 (H2 O)2]'
_chemical_formula_moiety         'C26 H24 Br2 N4 Ni O8'
_chemical_formula_sum            'C26 H24 Br2 N4 Ni O8'
_chemical_formula_weight         739.02
_chemical_name_systematic
Diaquabis(2-bromobenzoato-κO)bis(nicotinamide-κN¹)nickel(II)
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.609(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.8851(2)
_cell_length_b                   18.2865(4)
_cell_length_c                   9.7574(3)
_cell_measurement_reflns_used    5380
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      2.45
_cell_volume                     1348.23(6)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12686
_diffrn_reflns_theta_full        28.44
_diffrn_reflns_theta_max         28.44
_diffrn_reflns_theta_min         2.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.742
_exptl_absorpt_correction_T_max  0.436
_exptl_absorpt_correction_T_min  0.306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.479
_refine_diff_density_min         -0.554
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0538P)²+0.96P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                2899
_reflns_number_total             3368
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2538.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2222509
_cod_database_fobs_code          2222509
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'
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
Br Br1 0.40260(3) 0.212024(14) 0.17902(3) 0.02187(10) Uani d . 1 . .
Ni Ni1 0.5000 0.5000 0.5000 0.01048(11) Uani d S 1 . .
O O1 0.6201(2) 0.40537(9) 0.45455(18) 0.0137(3) Uani d . 1 . .
O O2 0.3946(2) 0.36790(10) 0.27275(19) 0.0162(4) Uani d . 1 . .
O O3 0.9542(2) 0.51033(10) 0.17931(19) 0.0184(4) Uani d . 1 . .
O O4 0.7554(2) 0.54252(10) 0.58888(19) 0.0149(4) Uani d . 1 . .
H H41 0.724(6) 0.574(2) 0.643(4) 0.045(11) Uiso d . 1 . .
H H42 0.838(5) 0.5193(19) 0.643(4) 0.024(8) Uiso d . 1 . .
N N1 0.5076(3) 0.54372(11) 0.3063(2) 0.0129(4) Uani d . 1 . .
N N2 0.8578(3) 0.57987(14) -0.0186(2) 0.0194(5) Uani d . 1 . .
H H21 0.776(5) 0.6019(19) -0.074(4) 0.034(10) Uiso d . 1 . .
H H22 0.935(5) 0.5647(18) -0.048(4) 0.023(8) Uiso d . 1 . .
C C1 0.5546(3) 0.36682(13) 0.3452(2) 0.0126(4) Uani d . 1 . .
C C2 0.6793(3) 0.31957(13) 0.2910(3) 0.0130(4) Uani d . 1 . .
C C3 0.6274(3) 0.25649(14) 0.2082(3) 0.0138(5) Uani d . 1 . .
C C4 0.7416(3) 0.22059(13) 0.1454(3) 0.0160(5) Uani d . 1 . .
H H4 0.7036 0.1793 0.0893 0.019 Uiso calc R 1 . .
C C5 0.9119(3) 0.24655(15) 0.1666(3) 0.0176(5) Uani d . 1 . .
H H5 0.9876 0.2235 0.1227 0.021 Uiso calc R 1 . .
C C6 0.9699(3) 0.30671(14) 0.2531(3) 0.0175(5) Uani d . 1 . .
H H6 1.0859 0.3230 0.2705 0.021 Uiso calc R 1 . .
C C7 0.8537(3) 0.34266(13) 0.3137(3) 0.0143(5) Uani d . 1 . .
H H7 0.8934 0.3833 0.3711 0.017 Uiso calc R 1 . .
C C8 0.3703(3) 0.58033(13) 0.2194(3) 0.0143(5) Uani d . 1 . .
H H8 0.2668 0.5848 0.2464 0.017 Uiso calc R 1 . .
C C9 0.3762(3) 0.61133(14) 0.0923(3) 0.0167(5) Uani d . 1 . .
H H9 0.2792 0.6367 0.0354 0.020 Uiso calc R 1 . .
C C10 0.5299(3) 0.60410(14) 0.0504(3) 0.0159(5) Uani d . 1 . .
H H10 0.5376 0.6246 -0.0348 0.019 Uiso calc R 1 . .
C C11 0.6709(3) 0.56580(13) 0.1378(3) 0.0131(5) Uani d . 1 . .
C C12 0.6545(3) 0.53690(13) 0.2651(3) 0.0134(5) Uani d . 1 . .
H H12 0.7500 0.5117 0.3243 0.016 Uiso calc R 1 . .
C C13 0.8401(3) 0.55041(14) 0.1008(3) 0.0152(5) Uani d . 1 . .
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'
Br Br -0.2901 2.4595 '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'
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_666 . 180.0000(10) ?
O1 Ni1 O4 . . 87.40(7) ?
O1 Ni1 O4 3_666 . 92.60(7) ?
O1 Ni1 O4 3_666 3_666 87.40(7) ?
O1 Ni1 O4 . 3_666 92.60(7) ?
O4 Ni1 O4 . 3_666 180.00(10) ?
N1 Ni1 O1 . . 89.60(7) ?
N1 Ni1 O1 3_666 . 90.40(7) ?
N1 Ni1 O1 . 3_666 90.40(7) ?
N1 Ni1 O1 3_666 3_666 89.60(7) ?
N1 Ni1 O4 . . 87.68(7) ?
N1 Ni1 O4 3_666 . 92.32(7) ?
N1 Ni1 O4 . 3_666 92.32(7) ?
N1 Ni1 O4 3_666 3_666 87.68(7) ?
N1 Ni1 N1 . 3_666 180.00(10) ?
C1 O1 Ni1 . . 122.99(15) ?
Ni1 O4 H41 . . 95(3) ?
Ni1 O4 H42 . . 124(2) ?
H42 O4 H41 . . 105(4) ?
C8 N1 Ni1 . . 122.66(15) ?
C12 N1 Ni1 . . 119.53(16) ?
C12 N1 C8 . . 117.8(2) ?
C13 N2 H21 . . 121(3) ?
C13 N2 H22 . . 118(2) ?
H21 N2 H22 . . 118(3) ?
O1 C1 C2 . . 117.8(2) ?
O2 C1 O1 . . 124.7(2) ?
O2 C1 C2 . . 117.4(2) ?
C3 C2 C1 . . 124.1(2) ?
C7 C2 C1 . . 118.8(2) ?
C7 C2 C3 . . 117.0(2) ?
C2 C3 Br1 . . 123.11(17) ?
C4 C3 Br1 . . 115.24(18) ?
C4 C3 C2 . . 121.6(2) ?
C3 C4 H4 . . 120.2 ?
C5 C4 C3 . . 119.7(2) ?
C5 C4 H4 . . 120.2 ?
C4 C5 H5 . . 119.9 ?
C6 C5 C4 . . 120.2(2) ?
C6 C5 H5 . . 119.9 ?
C5 C6 C7 . . 119.5(2) ?
C5 C6 H6 . . 120.3 ?
C7 C6 H6 . . 120.3 ?
C2 C7 H7 . . 119.0 ?
C6 C7 C2 . . 122.0(2) ?
C6 C7 H7 . . 119.0 ?
N1 C8 C9 . . 123.0(2) ?
N1 C8 H8 . . 118.5 ?
C9 C8 H8 . . 118.5 ?
C8 C9 C10 . . 118.8(2) ?
C8 C9 H9 . . 120.6 ?
C10 C9 H9 . . 120.6 ?
C9 C10 H10 . . 120.6 ?
C11 C10 C9 . . 118.8(2) ?
C11 C10 H10 . . 120.6 ?
C10 C11 C12 . . 118.7(2) ?
C10 C11 C13 . . 124.0(2) ?
C12 C11 C13 . . 117.3(2) ?
N1 C12 C11 . . 123.0(2) ?
N1 C12 H12 . . 118.5 ?
C11 C12 H12 . . 118.5 ?
O3 C13 N2 . . 122.8(2) ?
O3 C13 C11 . . 119.9(2) ?
N2 C13 C11 . . 117.2(2) ?
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
Br1 C3 . 1.896(2) ?
Ni1 O1 3_666 2.0806(16) ?
Ni1 O1 . 2.0806(16) yes
Ni1 O4 . 2.1012(17) yes
Ni1 O4 3_666 2.1012(17) ?
Ni1 N1 . 2.068(2) yes
Ni1 N1 3_666 2.068(2) ?
O1 C1 . 1.260(3) ?
O2 C1 . 1.258(3) ?
O3 C13 . 1.241(3) ?
O4 H41 . 0.86(4) ?
O4 H42 . 0.83(4) ?
N1 C8 . 1.347(3) ?
N1 C12 . 1.337(3) ?
N2 H21 . 0.82(4) ?
N2 H22 . 0.79(4) ?
C1 C2 . 1.513(3) ?
C2 C7 . 1.394(3) ?
C3 C2 . 1.400(4) ?
C3 C4 . 1.390(3) ?
C4 C5 . 1.383(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.382(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.390(3) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C8 . 1.377(3) ?
C9 H9 . 0.9300 ?
C10 C9 . 1.391(3) ?
C10 H10 . 0.9300 ?
C11 C10 . 1.383(3) ?
C11 C12 . 1.390(3) ?
C12 H12 . 0.9300 ?
C13 N2 . 1.327(3) ?
C13 C11 . 1.505(3) ?
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 3_665 0.82(4) 2.09(4) 2.864(3) 156(4) yes
N2 H22 O3 3_765 0.79(4) 2.22(4) 2.951(3) 153(4) yes
O4 H41 O2 3_666 0.86(4) 1.77(4) 2.612(2) 165(5) yes
O4 H42 O3 3_766 0.83(4) 2.09(4) 2.886(2) 162(3) yes
C9 H9 Cg1 3_556 0.93 2.89 3.617(3) 136 yes
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 . . . . -145.89(18) ?
O4 Ni1 O1 C1 3_666 . . . 34.11(18) ?
N1 Ni1 O1 C1 . . . . -58.20(18) ?
N1 Ni1 O1 C1 3_666 . . . 121.80(18) ?
O1 Ni1 N1 C8 . . . . 137.00(19) ?
O1 Ni1 N1 C8 3_666 . . . -43.00(19) ?
O1 Ni1 N1 C12 . . . . -44.08(18) ?
O1 Ni1 N1 C12 3_666 . . . 135.92(18) ?
O4 Ni1 N1 C12 . . . . 43.33(18) ?
O4 Ni1 N1 C12 3_666 . . . -136.67(18) ?
O4 Ni1 N1 C8 . . . . -135.59(19) ?
O4 Ni1 N1 C8 3_666 . . . 44.41(19) ?
Ni1 O1 C1 O2 . . . . -19.9(3) ?
Ni1 O1 C1 C2 . . . . 155.74(16) ?
Ni1 N1 C8 C9 . . . . 178.11(19) ?
C12 N1 C8 C9 . . . . -0.8(4) ?
Ni1 N1 C12 C11 . . . . -178.89(18) ?
C8 N1 C12 C11 . . . . 0.1(4) ?
O1 C1 C2 C3 . . . . 156.0(2) ?
O1 C1 C2 C7 . . . . -29.6(3) ?
O2 C1 C2 C3 . . . . -28.0(4) ?
O2 C1 C2 C7 . . . . 146.4(2) ?
C1 C2 C7 C6 . . . . -172.5(2) ?
C3 C2 C7 C6 . . . . 2.3(4) ?
Br1 C3 C2 C1 . . . . -10.9(3) ?
Br1 C3 C2 C7 . . . . 174.53(17) ?
C4 C3 C2 C1 . . . . 171.3(2) ?
C4 C3 C2 C7 . . . . -3.2(4) ?
Br1 C3 C4 C5 . . . . -176.67(19) ?
C2 C3 C4 C5 . . . . 1.2(4) ?
C3 C4 C5 C6 . . . . 1.7(4) ?
C4 C5 C6 C7 . . . . -2.6(4) ?
C5 C6 C7 C2 . . . . 0.5(4) ?
C10 C9 C8 N1 . . . . 0.7(4) ?
C11 C10 C9 C8 . . . . 0.2(4) ?
C12 C11 C10 C9 . . . . -0.9(4) ?
C13 C11 C10 C9 . . . . 176.4(2) ?
C10 C11 C12 N1 . . . . 0.8(4) ?
C13 C11 C12 N1 . . . . -176.7(2) ?
O3 C13 C11 C10 . . . . -173.8(2) ?
O3 C13 C11 C12 . . . . 3.5(4) ?
N2 C13 C11 C10 . . . . 4.7(4) ?
N2 C13 C11 C12 . . . . -178.0(2) ?
