#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/89/2228967.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_2228967
loop_
_publ_author_name
'Eshtiagh-Hosseini, Hossein'
'Alfi, Nafiseh'
'Mirzaei, Masoud'
'Fanwick, Philip E.'
_publ_section_title
;
 Bis(2-amino-6-methylpyridinium)
 trans-diaquabis(pyrazine-2,3-dicarboxylato)cobaltate(II)
 octahydrate
;
_journal_coeditor_code           BT5444
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m266
_journal_page_last               m267
_journal_paper_doi               10.1107/S1600536811001127
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac
'(C6 H9 N2)2 [Co (C6 H2 N2 O4)2 (H2 O)2], 8H2 O'
_chemical_formula_moiety
'2(C6 H9 N2 +), C12 H8 Co N4 O10 2-, 8 (H2 O)'
_chemical_formula_sum            'C24 H42 Co N8 O18'
_chemical_formula_weight         789.58
_chemical_name_systematic
;
Bis(2-amino-6-methylpyridinium)
trans-diaquabis(pyrazine-2,3-dicarboxylato)cobaltate(II)
octahydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                109.604(4)
_cell_angle_beta                 90.424(5)
_cell_angle_gamma                105.524(4)
_cell_formula_units_Z            1
_cell_length_a                   6.8570(4)
_cell_length_b                   10.2348(5)
_cell_length_c                   13.6403(10)
_cell_measurement_reflns_used    3181
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      71
_cell_measurement_theta_min      3
_cell_volume                     863.89(10)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection
'CrystalClear (Molecular Structure Corporation & Rigaku, 2001)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEP (Johnson, 1976) and
PLATON (Spek, 2009)
;
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution
;
SIR2004 (Burla et al., 2005)
;
_diffrn_ambient_temperature      150.0(2)
_diffrn_measured_fraction_theta_full 0.9260
_diffrn_measured_fraction_theta_max 0.9260
_diffrn_measurement_device_type  'Rigaku RAPID II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'confocal optics'
_diffrn_radiation_type           CU-K\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19137
_diffrn_reflns_theta_full        71.9
_diffrn_reflns_theta_max         71.89
_diffrn_reflns_theta_min         3.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.681
_exptl_absorpt_correction_T_max  0.5081
_exptl_absorpt_correction_T_min  0.2800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             413
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.40
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.030
_refine_ls_R_factor_gt           0.030
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0570P)²+0.2735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.087
_refine_ls_wR_factor_ref         0.087
_reflns_number_gt                3151
_reflns_number_total             3152
_reflns_threshold_expression     >2.0σ(I)
_cod_data_source_file            bt5444.cif
_cod_data_source_block           I
_cod_original_cell_volume        863.89(9)
_cod_original_formula_sum        'C24 H42 Co1 N8 O18'
_cod_database_code               2228967
_cod_database_fobs_code          2228967
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
Co1 1.0000 0.5000 0.0000 0.01861(12) Uani d S 1 . .
O1W 0.78751(19) 0.34893(13) -0.12293(10) 0.0281(3) Uani d . 1 . .
O21 0.79587(17) 0.45953(12) 0.10552(10) 0.0244(3) Uani d . 1 . .
O22 0.70494(18) 0.32395(14) 0.20508(10) 0.0309(3) Uani d . 1 . .
O2W 0.4756(2) 0.56148(13) 0.22356(12) 0.0277(3) Uani d . 1 . .
O31 0.97825(17) 0.20966(12) 0.31826(9) 0.0257(3) Uani d . 1 . .
O32 0.77764(18) 0.02378(12) 0.18707(10) 0.0278(3) Uani d . 1 . .
O3W 0.6610(2) 0.37101(15) 0.42401(11) 0.0318(3) Uani d . 1 . .
O4W 0.3166(2) 0.44434(16) 0.37295(12) 0.0307(3) Uani d . 1 . .
O5W 0.3645(2) 0.92255(14) 0.12233(11) 0.0301(3) Uani d . 1 . .
N1 1.08935(19) 0.33770(13) 0.03478(10) 0.0185(3) Uani d . 1 . .
N4 1.1850(2) 0.14113(14) 0.11111(11) 0.0212(3) Uani d . 1 . .
N11 0.82673(19) 0.07875(14) 0.46263(11) 0.0201(3) Uani d . 1 . .
N12 0.6818(2) -0.13230(16) 0.32292(12) 0.0243(3) Uani d . 1 . .
C2 0.9819(2) 0.29538(15) 0.10633(12) 0.0179(3) Uani d . 1 . .
C3 1.0303(2) 0.19613(16) 0.14422(13) 0.0188(3) Uani d . 1 . .
C5 1.2920(2) 0.18647(17) 0.04140(13) 0.0219(3) Uani d . 1 . .
C6 1.2436(2) 0.28428(17) 0.00249(13) 0.0213(3) Uani d . 1 . .
C12 0.7163(2) -0.06269(17) 0.42549(13) 0.0200(3) Uani d . 1 . .
C13 0.6442(2) -0.12847(18) 0.49910(14) 0.0240(4) Uani d . 1 . .
C14 0.6901(3) -0.0497(2) 0.60314(15) 0.0286(4) Uani d . 1 . .
C15 0.8071(3) 0.0960(2) 0.63821(14) 0.0281(4) Uani d . 1 . .
C16 0.8729(2) 0.15970(18) 0.56645(14) 0.0239(3) Uani d . 1 . .
C17 0.9948(3) 0.31426(18) 0.59367(16) 0.0307(4) Uani d . 1 . .
C21 0.8125(2) 0.36383(17) 0.14298(13) 0.0215(3) Uani d . 1 . .
C31 0.9158(2) 0.13968(17) 0.22335(13) 0.0211(3) Uani d . 1 . .
H5 1.4018 0.1516 0.0183 0.026 Uiso calc R 1 . .
H6 1.3200 0.3128 -0.0467 0.026 Uiso calc R 1 . .
H11 0.869(3) 0.117(2) 0.4202(17) 0.023(5) Uiso d . 1 . .
H13 0.5660 -0.2248 0.4768 0.029 Uiso calc R 1 . .
H14 0.6432 -0.0930 0.6518 0.034 Uiso calc R 1 . .
H15 0.8394 0.1485 0.7095 0.034 Uiso calc R 1 . .
H121 0.618(3) -0.223(3) 0.3014(17) 0.032(5) Uiso d . 1 . .
H122 0.716(3) -0.086(3) 0.2827(19) 0.035(6) Uiso d . 1 . .
H17A 1.1225 0.3185 0.5646 0.046 Uiso calc R 1 . .
H17B 1.0194 0.3600 0.6684 0.046 Uiso calc R 1 . .
H17C 0.9210 0.3636 0.5655 0.046 Uiso calc R 1 . .
H1W1 0.712(4) 0.374(3) -0.150(2) 0.044(7) Uiso d . 1 . .
H1W2 0.729(4) 0.263(3) -0.1249(19) 0.045(7) Uiso d . 1 . .
H2W1 0.561(4) 0.520(3) 0.191(2) 0.052(7) Uiso d . 1 . .
H2W2 0.431(4) 0.528(3) 0.260(2) 0.037(7) Uiso d . 1 . .
H3W1 0.728(4) 0.345(3) 0.378(2) 0.046(7) Uiso d . 1 . .
H3W2 0.564(4) 0.389(3) 0.399(2) 0.050(7) Uiso d . 1 . .
H4W1 0.300(4) 0.493(3) 0.430(2) 0.039(7) Uiso d . 1 . .
H4W2 0.219(4) 0.375(3) 0.356(2) 0.051(7) Uiso d . 1 . .
H5W1 0.478(4) 0.970(3) 0.145(2) 0.049(7) Uiso d . 1 . .
H5W2 0.304(4) 0.977(3) 0.125(2) 0.042(7) Uiso 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 0.0181 0.0091 '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'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O21 Co1 O21 2_765 . . 180.00(7) ?
O21 Co1 O1W 2_765 . . 90.50(5) ?
O21 Co1 O1W . . . 89.50(5) ?
O21 Co1 O1W 2_765 . 2_765 89.50(5) ?
O21 Co1 O1W . . 2_765 90.50(5) ?
O1W Co1 O1W . . 2_765 180.00(6) ?
O21 Co1 N1 2_765 . . 100.88(5) ?
O21 Co1 N1 . . . 79.12(5) ?
O1W Co1 N1 . . . 92.48(5) ?
O1W Co1 N1 2_765 . . 87.52(5) ?
O21 Co1 N1 2_765 . 2_765 79.12(5) ?
O21 Co1 N1 . . 2_765 100.88(5) ?
O1W Co1 N1 . . 2_765 87.52(5) ?
O1W Co1 N1 2_765 . 2_765 92.48(5) ?
N1 Co1 N1 . . 2_765 180.00(6) ?
Co1 O1W H1W1 . . . 119.7(19) ?
Co1 O1W H1W2 . . . 122.8(17) ?
H1W1 O1W H1W2 . . . 109(2) ?
C21 O21 Co1 . . . 116.29(10) ?
H2W1 O2W H2W2 . . . 110(3) ?
H3W1 O3W H3W2 . . . 108(3) ?
H4W1 O4W H4W2 . . . 104(3) ?
H5W1 O5W H5W2 . . . 106(3) ?
C6 N1 C2 . . . 118.50(13) ?
C6 N1 Co1 . . . 128.65(11) ?
C2 N1 Co1 . . . 112.57(10) ?
C5 N4 C3 . . . 117.44(13) ?
C12 N11 C16 . . . 123.77(15) ?
C12 N11 H11 . . . 117.9(15) ?
C16 N11 H11 . . . 118.3(15) ?
C12 N12 H121 . . . 117.3(15) ?
C12 N12 H122 . . . 119.2(16) ?
H121 N12 H122 . . . 123(2) ?
N1 C2 C3 . . . 120.37(14) ?
N1 C2 C21 . . . 116.14(13) ?
C3 C2 C21 . . . 123.47(14) ?
N4 C3 C2 . . . 121.24(14) ?
N4 C3 C31 . . . 114.49(13) ?
C2 C3 C31 . . . 124.27(14) ?
N4 C5 C6 . . . 121.69(14) ?
N4 C5 H5 . . . 119.20 ?
C6 C5 H5 . . . 119.20 ?
N1 C6 C5 . . . 120.75(14) ?
N1 C6 H6 . . . 119.60 ?
C5 C6 H6 . . . 119.60 ?
N12 C12 N11 . . . 119.07(15) ?
N12 C12 C13 . . . 123.23(15) ?
N11 C12 C13 . . . 117.70(15) ?
C14 C13 C12 . . . 119.36(15) ?
C14 C13 H13 . . . 120.30 ?
C12 C13 H13 . . . 120.30 ?
C13 C14 C15 . . . 121.07(16) ?
C13 C14 H14 . . . 119.50 ?
C15 C14 H14 . . . 119.50 ?
C16 C15 C14 . . . 119.19(17) ?
C16 C15 H15 . . . 120.40 ?
C14 C15 H15 . . . 120.40 ?
N11 C16 C15 . . . 118.88(15) ?
N11 C16 C17 . . . 116.76(16) ?
C15 C16 C17 . . . 124.35(17) ?
C16 C17 H17A . . . 109.50 ?
C16 C17 H17B . . . 109.50 ?
H17A C17 H17B . . . 109.50 ?
C16 C17 H17C . . . 109.50 ?
H17A C17 H17C . . . 109.50 ?
H17B C17 H17C . . . 109.50 ?
O22 C21 O21 . . . 125.85(15) ?
O22 C21 C2 . . . 118.38(14) ?
O21 C21 C2 . . . 115.77(13) ?
O32 C31 O31 . . . 126.69(15) ?
O32 C31 C3 . . . 116.34(15) ?
O31 C31 C3 . . . 116.80(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Co1 O21 . 2_765 2.0790(12) ?
Co1 O21 . . 2.0790(11) ?
Co1 O1W . . 2.0841(12) ?
Co1 O1W . 2_765 2.0841(12) ?
Co1 N1 . . 2.1045(12) ?
Co1 N1 . 2_765 2.1045(12) ?
O1W H1W1 . . 0.77(3) ?
O1W H1W2 . . 0.86(3) ?
O21 C21 . . 1.2760(19) ?
O22 C21 . . 1.228(2) ?
O2W H2W1 . . 0.85(3) ?
O2W H2W2 . . 0.72(3) ?
O31 C31 . . 1.256(2) ?
O32 C31 . . 1.244(2) ?
O3W H3W1 . . 0.80(3) ?
O3W H3W2 . . 0.84(3) ?
O4W H4W1 . . 0.80(3) ?
O4W H4W2 . . 0.80(3) ?
O5W H5W1 . . 0.79(3) ?
O5W H5W2 . . 0.77(3) ?
N1 C6 . . 1.329(2) ?
N1 C2 . . 1.344(2) ?
N4 C5 . . 1.335(2) ?
N4 C3 . . 1.342(2) ?
N11 C12 . . 1.357(2) ?
N11 C16 . . 1.363(2) ?
N11 H11 . . 0.82(2) ?
N12 C12 . . 1.325(2) ?
N12 H121 . . 0.86(2) ?
N12 H122 . . 0.84(2) ?
C2 C3 . . 1.393(2) ?
C2 C21 . . 1.516(2) ?
C3 C31 . . 1.518(2) ?
C5 C6 . . 1.388(2) ?
C5 H5 . . 0.9300 ?
C6 H6 . . 0.9300 ?
C12 C13 . . 1.410(2) ?
C13 C14 . . 1.361(3) ?
C13 H13 . . 0.9300 ?
C14 C15 . . 1.404(3) ?
C14 H14 . . 0.9300 ?
C15 C16 . . 1.365(3) ?
C15 H15 . . 0.9300 ?
C16 C17 . . 1.494(2) ?
C17 H17A . . 0.9600 ?
C17 H17B . . 0.9600 ?
C17 H17C . . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_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
N11 H11 O31 . . 0.82(2) 1.98(2) 2.794(3) 179(2) yes
N12 H121 O2W . 1_545 0.86(3) 2.05(2) 2.900(2) 170(2) yes
N12 H122 O32 . . 0.84(3) 1.97(3) 2.804(3) 176(2) yes
O1W H1W1 O2W . 2_665 0.78(3) 1.99(3) 2.770(3) 178(3) yes
O1W H1W2 O5W . 2_665 0.85(3) 1.85(3) 2.697(2) 172(3) yes
O2W H2W1 O21 . . 0.85(3) 2.10(3) 2.942(3) 168(3) yes
O2W H2W2 O4W . . 0.72(3) 2.07(3) 2.784(3) 176(2) yes
O3W H3W2 O4W . . 0.83(3) 1.99(3) 2.811(3) 167(3) yes
O4W H4W1 O3W . 2_666 0.80(3) 1.98(2) 2.755(2) 165(3) yes
O4W H4W2 O31 . 1_455 0.80(2) 1.94(2) 2.738(2) 178(3) yes
O5W H5W1 O32 . 1_565 0.79(2) 2.00(3) 2.767(2) 161(3) yes
O5W H5W2 N4 . 1_465 0.77(3) 2.11(3) 2.871(3) 167(3) 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
O21 Co1 O21 C21 2_765 . . . 11E1(5) ?
O1W Co1 O21 C21 . . . . 93.19(12) ?
O1W Co1 O21 C21 2_765 . . . -86.81(12) ?
N1 Co1 O21 C21 . . . . 0.57(11) ?
N1 Co1 O21 C21 2_765 . . . -179.43(11) ?
O21 Co1 N1 C6 2_765 . . . 3.94(14) ?
O21 Co1 N1 C6 . . . . -176.06(14) ?
O1W Co1 N1 C6 . . . . 94.93(14) ?
O1W Co1 N1 C6 2_765 . . . -85.07(14) ?
N1 Co1 N1 C6 2_765 . . . 9E1(6) ?
O21 Co1 N1 C2 2_765 . . . 177.76(10) ?
O21 Co1 N1 C2 . . . . -2.24(10) ?
O1W Co1 N1 C2 . . . . -91.26(11) ?
O1W Co1 N1 C2 2_765 . . . 88.74(11) ?
N1 Co1 N1 C2 2_765 . . . -10E1(6) ?
C6 N1 C2 C3 . . . . -0.9(2) ?
Co1 N1 C2 C3 . . . . -175.43(11) ?
C6 N1 C2 C21 . . . . 177.95(13) ?
Co1 N1 C2 C21 . . . . 3.44(16) ?
C5 N4 C3 C2 . . . . 0.7(2) ?
C5 N4 C3 C31 . . . . -179.98(13) ?
N1 C2 C3 N4 . . . . 0.4(2) ?
C21 C2 C3 N4 . . . . -178.37(14) ?
N1 C2 C3 C31 . . . . -178.80(14) ?
C21 C2 C3 C31 . . . . 2.4(2) ?
C3 N4 C5 C6 . . . . -1.4(2) ?
C2 N1 C6 C5 . . . . 0.3(2) ?
Co1 N1 C6 C5 . . . . 173.81(11) ?
N4 C5 C6 N1 . . . . 0.9(2) ?
C16 N11 C12 N12 . . . . -179.22(14) ?
C16 N11 C12 C13 . . . . 0.6(2) ?
N12 C12 C13 C14 . . . . 178.72(15) ?
N11 C12 C13 C14 . . . . -1.1(2) ?
C12 C13 C14 C15 . . . . 0.3(2) ?
C13 C14 C15 C16 . . . . 1.0(2) ?
C12 N11 C16 C15 . . . . 0.7(2) ?
C12 N11 C16 C17 . . . . -179.59(14) ?
C14 C15 C16 N11 . . . . -1.5(2) ?
C14 C15 C16 C17 . . . . 178.83(15) ?
Co1 O21 C21 O22 . . . . -179.10(14) ?
Co1 O21 C21 C2 . . . . 1.06(18) ?
N1 C2 C21 O22 . . . . 177.04(14) ?
C3 C2 C21 O22 . . . . -4.1(2) ?
N1 C2 C21 O21 . . . . -3.1(2) ?
C3 C2 C21 O21 . . . . 175.73(14) ?
N4 C3 C31 O32 . . . . -85.16(17) ?
C2 C3 C31 O32 . . . . 94.11(19) ?
N4 C3 C31 O31 . . . . 90.54(17) ?
C2 C3 C31 O31 . . . . -90.20(19) ?
