#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/60/2226040.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_2226040
loop_
_publ_author_name
'Tabatabaee, Masoumeh'
_publ_section_title
;
 (2-Aminopyrimidine-κN¹)diaqua(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)nickel(II)
 monohydrate
;
_journal_coeditor_code           BH2281
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m647
_journal_page_last               m648
_journal_paper_doi               10.1107/S1600536810016843
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Ni (C7 H3 N O4) (C4 H5 N3) (H2 O)2], H2 O'
_chemical_formula_moiety         'C11 H12 N4 Ni O6, H2 O'
_chemical_formula_sum            'C11 H14 N4 Ni O7'
_chemical_formula_weight         372.97
_chemical_name_systematic
;
(2-Aminopyrimidine-κN¹)diaqua(pyridine-2,6-dicarboxylato-
κ³O²,N,O⁶)nickel(II) monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 102.677(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6073(8)
_cell_length_b                   10.2038(10)
_cell_length_c                   14.6095(15)
_cell_measurement_reflns_used    896
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.89
_cell_volume                     1397.3(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12010
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    1.435
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.510
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0556
_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)+(0.07P)²+9.0P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1625
_reflns_number_gt                2396
_reflns_number_total             2725
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2281.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226040
_cod_database_fobs_code          2226040
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'
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 0.71391(7) 0.20931(6) 0.07096(4) 0.0268(2) Uani d . 1 . .
N N1 0.7944(4) 0.0931(3) 0.1775(2) 0.0212(8) Uani d . 1 . .
N N2 0.6262(5) 0.3303(4) -0.0398(3) 0.0364(11) Uani d . 1 . .
N N3 0.5712(6) 0.5362(6) -0.1177(3) 0.0574(17) Uani d . 1 . .
N N4 0.7236(6) 0.5244(4) 0.0275(3) 0.0451(13) Uani d . 1 . .
H H4B 0.7678 0.4812 0.0758 0.054 Uiso calc R 1 . .
H H4C 0.7332 0.6080 0.0254 0.054 Uiso calc R 1 . .
O O1 0.7779(4) 0.3446(3) 0.1821(2) 0.0328(8) Uani d . 1 . .
O O2 0.8528(5) 0.3529(3) 0.3379(2) 0.0395(9) Uani d . 1 . .
O O3 0.6800(4) 0.0198(4) 0.0080(2) 0.0328(8) Uani d . 1 . .
O O4 0.7485(7) -0.1853(4) 0.0367(3) 0.0740(18) Uani d . 1 . .
C C1 0.8233(6) 0.2929(4) 0.2627(3) 0.0289(11) Uani d . 1 . .
C C2 0.8404(5) 0.1458(4) 0.2621(3) 0.0229(9) Uani d . 1 . .
C C3 0.8944(5) 0.0683(5) 0.3388(3) 0.0290(10) Uani d . 1 . .
H H3A 0.9272 0.1048 0.3979 0.035 Uiso calc R 1 . .
C C4 0.8982(6) -0.0660(5) 0.3249(4) 0.0376(12) Uani d . 1 . .
H H4A 0.9347 -0.1210 0.3753 0.045 Uiso calc R 1 . .
C C5 0.8481(7) -0.1188(5) 0.2367(4) 0.0394(13) Uani d . 1 . .
H H5A 0.8490 -0.2088 0.2272 0.047 Uiso calc R 1 . .
C C6 0.7967(5) -0.0346(4) 0.1630(3) 0.0271(10) Uani d . 1 . .
C C7 0.7374(5) -0.0716(5) 0.0620(3) 0.0307(11) Uani d . 1 . .
C C8 0.6402(7) 0.4615(6) -0.0441(3) 0.0416(15) Uani d . 1 . .
C C9 0.5438(7) 0.2718(7) -0.1134(4) 0.0497(17) Uani d . 1 . .
H H9A 0.5343 0.1812 -0.1121 0.060 Uiso calc R 1 . .
C C10 0.4716(7) 0.3385(8) -0.1914(4) 0.060(2) Uani d . 1 . .
H H10A 0.4143 0.2962 -0.2424 0.072 Uiso calc R 1 . .
C C11 0.4907(8) 0.4728(8) -0.1885(4) 0.068(3) Uani d . 1 . .
H H11A 0.4436 0.5216 -0.2397 0.082 Uiso calc R 1 . .
O O1W 0.5159(4) 0.2003(4) 0.1048(2) 0.0419(10) Uani d . 1 . .
H H1 0.4722 0.1549 0.0585 0.063 Uiso d R 1 . .
H H2 0.4721 0.2693 0.1148 0.063 Uiso d R 1 . .
O O2W 0.9039(4) 0.2190(3) 0.0257(2) 0.0266(7) Uani d . 1 . .
H H3 0.8894 0.1987 -0.0320 0.040 Uiso d R 1 . .
H H4 0.9753 0.1835 0.0619 0.040 Uiso d R 1 . .
O O3W 0.1432(4) 0.1177(3) 0.1323(2) 0.0320(8) Uani d . 1 . .
H H5 0.1465 0.0351 0.1402 0.048 Uiso d R 1 . .
H H6 0.1922 0.1248 0.0907 0.048 Uiso d R 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'
Ni Ni 0.3393 1.1124 '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
N1 Ni1 N2 . . 178.94(18) ?
N1 Ni1 O1W . . 90.35(15) ?
N2 Ni1 O1W . . 88.59(17) ?
N1 Ni1 O2W . . 93.46(14) ?
N2 Ni1 O2W . . 87.59(16) ?
O1W Ni1 O2W . . 175.37(12) ?
N1 Ni1 O1 . . 77.84(13) ?
N2 Ni1 O1 . . 102.19(15) ?
O1W Ni1 O1 . . 88.48(15) ?
O2W Ni1 O1 . . 94.88(13) ?
N1 Ni1 O3 . . 78.02(13) ?
N2 Ni1 O3 . . 101.92(15) ?
O1W Ni1 O3 . . 90.07(15) ?
O2W Ni1 O3 . . 88.15(13) ?
O1 Ni1 O3 . . 155.80(13) ?
C6 N1 C2 . . 122.3(4) ?
C6 N1 Ni1 . . 118.9(3) ?
C2 N1 Ni1 . . 118.8(3) ?
C9 N2 C8 . . 117.1(5) ?
C9 N2 Ni1 . . 115.7(4) ?
C8 N2 Ni1 . . 127.1(4) ?
C11 N3 C8 . . 116.4(6) ?
C8 N4 H4B . . 120.0 ?
C8 N4 H4C . . 120.0 ?
H4B N4 H4C . . 120.0 ?
C1 O1 Ni1 . . 114.9(3) ?
C7 O3 Ni1 . . 113.2(3) ?
O2 C1 O1 . . 125.5(4) ?
O2 C1 C2 . . 119.6(4) ?
O1 C1 C2 . . 114.8(4) ?
N1 C2 C3 . . 120.9(4) ?
N1 C2 C1 . . 113.2(4) ?
C3 C2 C1 . . 126.0(4) ?
C2 C3 C4 . . 117.7(4) ?
C2 C3 H3A . . 121.1 ?
C4 C3 H3A . . 121.1 ?
C5 C4 C3 . . 120.4(5) ?
C5 C4 H4A . . 119.8 ?
C3 C4 H4A . . 119.8 ?
C6 C5 C4 . . 118.5(5) ?
C6 C5 H5A . . 120.8 ?
C4 C5 H5A . . 120.8 ?
N1 C6 C5 . . 120.2(4) ?
N1 C6 C7 . . 112.9(4) ?
C5 C6 C7 . . 126.9(4) ?
O4 C7 O3 . . 124.2(5) ?
O4 C7 C6 . . 119.4(5) ?
O3 C7 C6 . . 116.4(4) ?
N4 C8 N2 . . 119.3(4) ?
N4 C8 N3 . . 117.0(6) ?
N2 C8 N3 . . 123.7(6) ?
N2 C9 C10 . . 123.4(7) ?
N2 C9 H9A . . 118.3 ?
C10 C9 H9A . . 118.3 ?
C9 C10 C11 . . 115.1(6) ?
C9 C10 H10A . . 122.4 ?
C11 C10 H10A . . 122.4 ?
N3 C11 C10 . . 124.2(5) ?
N3 C11 H11A . . 117.9 ?
C10 C11 H11A . . 117.9 ?
Ni1 O1W H1 . . 98.9 ?
Ni1 O1W H2 . . 121.3 ?
H1 O1W H2 . . 114.3 ?
Ni1 O2W H3 . . 109.9 ?
Ni1 O2W H4 . . 115.4 ?
H3 O2W H4 . . 116.5 ?
H5 O3W H6 . . 99.9 ?
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 . 1.975(4) ?
Ni1 N2 . 2.062(4) ?
Ni1 O1W . 2.070(4) ?
Ni1 O2W . 2.076(4) ?
Ni1 O1 . 2.117(3) ?
Ni1 O3 . 2.136(4) ?
N1 C6 . 1.321(6) ?
N1 C2 . 1.330(5) ?
N2 C9 . 1.329(7) ?
N2 C8 . 1.348(8) ?
N3 C11 . 1.317(10) ?
N3 C8 . 1.365(6) ?
N4 C8 . 1.334(8) ?
N4 H4B . 0.8600 ?
N4 H4C . 0.8600 ?
O1 C1 . 1.278(5) ?
O2 C1 . 1.235(6) ?
O3 C7 . 1.267(6) ?
O4 C7 . 1.230(6) ?
C1 C2 . 1.510(6) ?
C2 C3 . 1.377(6) ?
C3 C4 . 1.388(7) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.382(7) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.381(7) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.509(6) ?
C9 C10 . 1.377(8) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.382(12) ?
C10 H10A . 0.9300 ?
C11 H11A . 0.9300 ?
O1W H1 . 0.8500 ?
O1W H2 . 0.8499 ?
O2W H3 . 0.8500 ?
O2W H4 . 0.8500 ?
O3W H5 . 0.8500 ?
O3W H6 . 0.8500 ?
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
N4 H4B O1 1_555 0.86 2.073 2.867(5) 153 yes
N4 H4C O4 1_565 0.86 2.117 2.973(6) 173 yes
O1W H1 O4 3_655 0.85 2.287 2.906(7) 130 yes
O1W H1 O3 3_655 0.85 2.374 3.152(5) 152 yes
O1W H2 N3 3_665 0.85 2.030 2.835(7) 158 no
O2W H3 O2 4_565 0.85 1.928 2.777(4) 178 yes
O2W H4 O3W 1_655 0.85 1.839 2.685(5) 173 yes
O3W H5 O2 2_645 0.85 1.887 2.736(4) 177 yes
O3W H6 O4 3_655 0.85 2.153 2.964(6) 159 yes
O3W H6 O3 3_655 0.85 2.557 3.253(5) 140 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
O1W Ni1 N1 C6 . . . . 92.7(4) ?
O2W Ni1 N1 C6 . . . . -84.7(4) ?
O1 Ni1 N1 C6 . . . . -179.0(4) ?
O3 Ni1 N1 C6 . . . . 2.7(3) ?
O1W Ni1 N1 C2 . . . . -85.3(3) ?
O2W Ni1 N1 C2 . . . . 97.3(3) ?
O1 Ni1 N1 C2 . . . . 3.0(3) ?
O3 Ni1 N1 C2 . . . . -175.3(4) ?
O1W Ni1 N2 C9 . . . . -75.1(4) ?
O2W Ni1 N2 C9 . . . . 102.3(4) ?
O1 Ni1 N2 C9 . . . . -163.2(4) ?
O3 Ni1 N2 C9 . . . . 14.7(4) ?
O1W Ni1 N2 C8 . . . . 102.8(5) ?
O2W Ni1 N2 C8 . . . . -79.8(5) ?
O1 Ni1 N2 C8 . . . . 14.7(5) ?
O3 Ni1 N2 C8 . . . . -167.4(4) ?
N1 Ni1 O1 C1 . . . . -5.9(4) ?
N2 Ni1 O1 C1 . . . . 173.0(4) ?
O1W Ni1 O1 C1 . . . . 84.8(4) ?
O2W Ni1 O1 C1 . . . . -98.4(4) ?
O3 Ni1 O1 C1 . . . . -2.0(6) ?
N1 Ni1 O3 C7 . . . . -6.9(3) ?
N2 Ni1 O3 C7 . . . . 174.2(3) ?
O1W Ni1 O3 C7 . . . . -97.2(3) ?
O2W Ni1 O3 C7 . . . . 87.1(3) ?
O1 Ni1 O3 C7 . . . . -10.7(6) ?
Ni1 O1 C1 O2 . . . . -172.6(5) ?
Ni1 O1 C1 C2 . . . . 7.4(6) ?
C6 N1 C2 C3 . . . . 0.6(7) ?
Ni1 N1 C2 C3 . . . . 178.6(4) ?
C6 N1 C2 C1 . . . . -178.1(4) ?
Ni1 N1 C2 C1 . . . . -0.2(5) ?
O2 C1 C2 N1 . . . . 175.1(5) ?
O1 C1 C2 N1 . . . . -5.0(6) ?
O2 C1 C2 C3 . . . . -3.6(8) ?
O1 C1 C2 C3 . . . . 176.3(5) ?
N1 C2 C3 C4 . . . . -0.4(7) ?
C1 C2 C3 C4 . . . . 178.2(5) ?
C2 C3 C4 C5 . . . . -0.5(8) ?
C3 C4 C5 C6 . . . . 1.1(9) ?
C2 N1 C6 C5 . . . . 0.0(7) ?
Ni1 N1 C6 C5 . . . . -177.9(4) ?
C2 N1 C6 C7 . . . . 179.2(4) ?
Ni1 N1 C6 C7 . . . . 1.3(5) ?
C4 C5 C6 N1 . . . . -0.8(8) ?
C4 C5 C6 C7 . . . . -179.9(5) ?
Ni1 O3 C7 O4 . . . . -169.6(5) ?
Ni1 O3 C7 C6 . . . . 9.5(5) ?
N1 C6 C7 O4 . . . . 171.6(5) ?
C5 C6 C7 O4 . . . . -9.3(8) ?
N1 C6 C7 O3 . . . . -7.5(6) ?
C5 C6 C7 O3 . . . . 171.6(5) ?
C9 N2 C8 N4 . . . . -179.0(5) ?
Ni1 N2 C8 N4 . . . . 3.2(7) ?
C9 N2 C8 N3 . . . . 2.3(8) ?
Ni1 N2 C8 N3 . . . . -175.6(4) ?
C11 N3 C8 N4 . . . . 179.1(5) ?
C11 N3 C8 N2 . . . . -2.1(8) ?
C8 N2 C9 C10 . . . . -1.2(9) ?
Ni1 N2 C9 C10 . . . . 176.9(5) ?
N2 C9 C10 C11 . . . . 0.0(9) ?
C8 N3 C11 C10 . . . . 0.8(9) ?
C9 C10 C11 N3 . . . . 0.2(9) ?
