#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/12/2221228.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_2221228
loop_
_publ_author_name
'Özbek, F. Elif'
'Tercan, Barış'
'Şahin, Ertan'
'Necefoğlu, Hacali'
'Hökelek, Tuncer'
_publ_section_title
;
 Tetraaquabis(nicotinamide-κN¹)cobalt(II)
 bis(2-fluorobenzoate)
;
_journal_coeditor_code           XU2482
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m341
_journal_page_last               m342
_journal_paper_doi               10.1107/S1600536809006771
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Co (C6 H6 N2 O)2 (H2 O)4] (C7 H4 F O2)2'
_chemical_formula_moiety         'C12 H20 Co N4 O6 2+, 2(C7 H4 F O2 -)'
_chemical_formula_sum            'C26 H28 Co F2 N4 O10'
_chemical_formula_weight         653.45
_chemical_name_systematic
;
Tetraaquabis(nicotinamide-κN¹)cobalt(II) bis(2-fluorobenzoate)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.160(2)
_cell_angle_beta                 77.275(3)
_cell_angle_gamma                63.740(3)
_cell_formula_units_Z            1
_cell_length_a                   7.2913(2)
_cell_length_b                   7.4522(4)
_cell_length_c                   14.4853(5)
_cell_measurement_reflns_used    4045
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.3714
_cell_measurement_theta_min      2.8861
_cell_volume                     687.83(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'Mercury (Macrae et al.,  2006)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID-S'
_diffrn_measurement_method       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  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14875
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             337
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.369
_refine_diff_density_min         -0.423
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2817
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.512
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0421
_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)+(0.0649P)²+0.4285P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                2679
_reflns_number_total             2817
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2482.cif
_cod_data_source_block           I
_cod_database_code               2221228
_cod_database_fobs_code          2221228
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Co Co1 0.5000 0.5000 0.5000 0.0306(2) Uani d S 1 . .
F F1 0.6929(4) 0.9615(4) 0.85873(18) 0.0632(7) Uani d . 1 . .
O O1 0.2777(4) 0.4281(5) 0.97121(18) 0.0544(7) Uani d . 1 . .
O O2 0.9068(4) 0.8007(4) 0.68460(17) 0.0433(6) Uani d . 1 . .
O O3 0.7033(4) 0.9537(4) 0.57755(17) 0.0414(6) Uani d . 1 . .
O O4 0.6387(4) 0.7065(4) 0.46282(17) 0.0398(6) Uani d D 1 . .
H H41 0.695(6) 0.741(6) 0.504(3) 0.057(13) Uiso d D 1 . .
H H42 0.529(7) 0.818(6) 0.449(4) 0.10(2) Uiso d D 1 . .
O O5 0.7856(4) 0.2570(4) 0.46679(18) 0.0450(6) Uani d D 1 . .
H H51 0.896(5) 0.227(7) 0.419(3) 0.070(15) Uiso d D 1 . .
H H52 0.799(7) 0.140(5) 0.499(3) 0.053(12) Uiso d D 1 . .
N N1 0.5506(4) 0.4540(4) 0.64340(18) 0.0334(6) Uani d . 1 . .
N N2 0.0471(5) 0.5743(5) 0.8720(2) 0.0460(8) Uani d D 1 . .
H H21 -0.056(5) 0.588(6) 0.918(2) 0.047(11) Uiso d D 1 . .
H H22 0.019(6) 0.640(5) 0.819(2) 0.041(10) Uiso d D 1 . .
C C1 0.3949(5) 0.4742(5) 0.7168(2) 0.0337(7) Uani d . 1 . .
H H1 0.2679 0.4926 0.7042 0.040 Uiso calc R 1 . .
C C2 0.4139(5) 0.4691(5) 0.8104(2) 0.0348(7) Uani d . 1 . .
C C3 0.6044(6) 0.4392(5) 0.8293(2) 0.0393(8) Uani d . 1 . .
H H3 0.6229 0.4340 0.8913 0.047 Uiso calc R 1 . .
C C4 0.7650(5) 0.4175(5) 0.7546(3) 0.0408(8) Uani d . 1 . .
H H4 0.8937 0.3981 0.7654 0.049 Uiso calc R 1 . .
C C5 0.7332(5) 0.4248(5) 0.6634(2) 0.0380(7) Uani d . 1 . .
H H5 0.8434 0.4089 0.6135 0.046 Uiso calc R 1 . .
C C6 0.2384(6) 0.4906(6) 0.8914(2) 0.0393(8) Uani d . 1 . .
C C7 0.7326(5) 0.8934(5) 0.6617(2) 0.0326(7) Uani d . 1 . .
C C8 0.5407(5) 0.9340(5) 0.7363(2) 0.0330(7) Uani d . 1 . .
C C9 0.3610(5) 0.9450(5) 0.7114(3) 0.0381(7) Uani d . 1 . .
H H9 0.3613 0.9304 0.6486 0.046 Uiso calc R 1 . .
C C10 0.1833(6) 0.9768(6) 0.7779(3) 0.0474(9) Uani d . 1 . .
H H10 0.0663 0.9813 0.7601 0.057 Uiso calc R 1 . .
C C11 0.1798(7) 1.0021(7) 0.8708(3) 0.0572(11) Uani d . 1 . .
H H11 0.0593 1.0261 0.9155 0.069 Uiso calc R 1 . .
C C12 0.3539(7) 0.9920(7) 0.8980(3) 0.0544(10) Uani d . 1 . .
H H12 0.3526 1.0070 0.9609 0.065 Uiso calc R 1 . .
C C13 0.5296(6) 0.9593(6) 0.8305(2) 0.0411(8) 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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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
O4 Co1 O4 2_666 . 180.0 ?
O4 Co1 N1 2_666 . 86.31(10) ?
O4 Co1 N1 . . 93.69(10) yes
O4 Co1 N1 2_666 2_666 93.69(10) ?
O4 Co1 N1 . 2_666 86.31(10) yes
O5 Co1 O4 2_666 2_666 91.75(12) ?
O5 Co1 O4 . 2_666 88.25(12) ?
O5 Co1 O4 2_666 . 88.25(12) yes
O5 Co1 O4 . . 91.75(12) yes
O5 Co1 O5 2_666 . 180.0 ?
O5 Co1 N1 2_666 . 92.59(11) yes
O5 Co1 N1 . . 87.41(11) yes
O5 Co1 N1 2_666 2_666 87.41(11) ?
O5 Co1 N1 . 2_666 92.59(11) ?
N1 Co1 N1 . 2_666 180.0000(10) ?
Co1 O4 H41 . . 124(3) ?
Co1 O4 H42 . . 101(4) ?
H41 O4 H42 . . 106(3) ?
Co1 O5 H51 . . 136(3) ?
Co1 O5 H52 . . 116(3) ?
H51 O5 H52 . . 107(3) ?
C1 N1 Co1 . . 121.3(2) ?
C5 N1 C1 . . 117.3(3) ?
C5 N1 Co1 . . 121.1(2) ?
C6 N2 H21 . . 118(3) ?
C6 N2 H22 . . 122(3) ?
H21 N2 H22 . . 118(4) ?
N1 C1 C2 . . 123.3(3) ?
N1 C1 H1 . . 118.3 ?
C2 C1 H1 . . 118.3 ?
C1 C2 C3 . . 118.4(3) ?
C1 C2 C6 . . 122.5(3) ?
C3 C2 C6 . . 119.1(3) ?
C2 C3 H3 . . 120.6 ?
C4 C3 C2 . . 118.7(3) ?
C4 C3 H3 . . 120.6 ?
C3 C4 C5 . . 119.3(3) ?
C3 C4 H4 . . 120.3 ?
C5 C4 H4 . . 120.3 ?
N1 C5 C4 . . 123.0(3) ?
N1 C5 H5 . . 118.5 ?
C4 C5 H5 . . 118.5 ?
O1 C6 N2 . . 123.5(3) ?
O1 C6 C2 . . 119.1(3) ?
N2 C6 C2 . . 117.3(3) ?
O2 C7 O3 . . 124.3(3) ?
O2 C7 C8 . . 119.3(3) ?
O3 C7 C8 . . 116.3(3) ?
C9 C8 C7 . . 119.6(3) ?
C13 C8 C7 . . 123.9(3) ?
C13 C8 C9 . . 116.5(3) ?
C8 C9 H9 . . 119.2 ?
C10 C9 C8 . . 121.5(3) ?
C10 C9 H9 . . 119.2 ?
C9 C10 H10 . . 120.1 ?
C11 C10 C9 . . 119.7(4) ?
C11 C10 H10 . . 120.1 ?
C10 C11 C12 . . 120.4(4) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C11 C12 H12 . . 120.6 ?
C13 C12 C11 . . 118.8(4) ?
C13 C12 H12 . . 120.6 ?
F1 C13 C12 . . 117.1(3) ?
F1 C13 C8 . . 119.8(3) ?
C12 C13 C8 . . 123.0(4) ?
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
Co1 O4 2_666 2.143(3) ?
Co1 O4 . 2.143(3) yes
Co1 O5 2_666 2.075(3) ?
Co1 O5 . 2.075(3) yes
Co1 N1 . 2.145(3) yes
Co1 N1 2_666 2.145(3) ?
F1 C13 . 1.348(4) ?
O1 C6 . 1.232(4) ?
O2 C7 . 1.244(4) ?
O3 C7 . 1.270(4) ?
O4 H41 . 0.91(5) ?
O4 H42 . 0.90(3) ?
O5 H51 . 0.90(4) ?
O5 H52 . 0.91(2) ?
N1 C1 . 1.342(4) ?
N1 C5 . 1.342(4) ?
N2 C6 . 1.330(5) ?
N2 H21 . 0.87(2) ?
N2 H22 . 0.87(2) ?
C1 H1 . 0.9300 ?
C2 C1 . 1.387(4) ?
C2 C3 . 1.390(5) ?
C3 H3 . 0.9300 ?
C4 C3 . 1.375(5) ?
C4 H4 . 0.9300 ?
C5 C4 . 1.381(5) ?
C5 H5 . 0.9300 ?
C6 C2 . 1.499(5) ?
C7 C8 . 1.505(5) ?
C8 C9 . 1.399(5) ?
C8 C13 . 1.384(5) ?
C9 C10 . 1.379(5) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C10 . 1.377(6) ?
C11 H11 . 0.9300 ?
C12 C11 . 1.378(6) ?
C12 C13 . 1.376(5) ?
C12 H12 . 0.9300 ?
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 O1 2_567 0.87(2) 2.04(3) 2.902(5) 171(4) yes
N2 H22 F1 1_455 0.87(2) 2.54(4) 2.916(5) 107(2) yes
N2 H22 O2 1_455 0.87(2) 2.26(3) 3.116(5) 172(4) yes
O4 H41 O3 . 0.91(5) 2.06(4) 2.885(4) 151(4) yes
O4 H42 O3 2_676 0.90(3) 1.86(5) 2.761(4) 178(5) yes
O5 H51 O2 2_766 0.90(4) 1.80(4) 2.695(4) 172(4) yes
O5 H52 O3 1_545 0.91(2) 1.95(4) 2.798(4) 156(4) 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 Co1 N1 C1 2_666 . . . -51.9(3) ?
O4 Co1 N1 C1 . . . . 128.1(3) ?
O4 Co1 N1 C5 2_666 . . . 135.3(3) ?
O4 Co1 N1 C5 . . . . -44.7(3) ?
O5 Co1 N1 C1 2_666 . . . 39.7(3) ?
O5 Co1 N1 C1 . . . . -140.3(3) ?
O5 Co1 N1 C5 2_666 . . . -133.1(3) ?
O5 Co1 N1 C5 . . . . 46.9(3) ?
Co1 N1 C1 C2 . . . . -172.2(3) ?
C5 N1 C1 C2 . . . . 0.9(5) ?
Co1 N1 C5 C4 . . . . 172.4(3) ?
C1 N1 C5 C4 . . . . -0.8(5) ?
C3 C2 C1 N1 . . . . -0.8(5) ?
C6 C2 C1 N1 . . . . -179.5(3) ?
C1 C2 C3 C4 . . . . 0.5(5) ?
C6 C2 C3 C4 . . . . 179.3(3) ?
C5 C4 C3 C2 . . . . -0.4(5) ?
N1 C5 C4 C3 . . . . 0.5(6) ?
O1 C6 C2 C1 . . . . 158.9(4) ?
O1 C6 C2 C3 . . . . -19.9(5) ?
N2 C6 C2 C1 . . . . -20.0(5) ?
N2 C6 C2 C3 . . . . 161.2(3) ?
O2 C7 C8 C9 . . . . -149.0(3) ?
O2 C7 C8 C13 . . . . 30.0(5) ?
O3 C7 C8 C9 . . . . 29.2(4) ?
O3 C7 C8 C13 . . . . -151.7(3) ?
C7 C8 C9 C10 . . . . 178.3(3) ?
C13 C8 C9 C10 . . . . -0.8(5) ?
C7 C8 C13 F1 . . . . 4.5(5) ?
C7 C8 C13 C12 . . . . -178.5(4) ?
C9 C8 C13 F1 . . . . -176.4(3) ?
C9 C8 C13 C12 . . . . 0.5(6) ?
C8 C9 C10 C11 . . . . 1.1(6) ?
C12 C11 C10 C9 . . . . -1.2(7) ?
C11 C12 C13 F1 . . . . 176.4(4) ?
C11 C12 C13 C8 . . . . -0.6(7) ?
C13 C12 C11 C10 . . . . 1.0(7) ?
