#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/09/2200917.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_2200917
loop_
_publ_author_name
'Odoko, Mamiko'
'Adachi, Yukari'
'Okabe, Nobuo'
_publ_section_title
;
 Bis[2-hydroxy-3-(1H-imidazol-4-yl)propionato]nickel(II)
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m7
_journal_page_last               m9
_journal_paper_doi               10.1107/S1600536801020335
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          '[Ni (C6 H7 N2 O3)2]'
_chemical_formula_moiety         'C12 H14 N4 Ni O6'
_chemical_formula_sum            'C12 H14 N4 Ni O6'
_chemical_formula_weight         368.96
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.631(3)
_cell_length_b                   13.283(3)
_cell_length_c                   5.214(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      24.7
_cell_volume                     736.3(5)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation & Rigaku, 1999)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC-5R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .7107
_diffrn_reflns_av_R_equivalents  .000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1018
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_decay_%        .46
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.355
_exptl_absorpt_correction_T_max  .666
_exptl_absorpt_correction_T_min  .621
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            light_blue
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pillar
_exptl_crystal_F_000             380.0
_exptl_crystal_size_max          .500
_exptl_crystal_size_mid          .300
_exptl_crystal_size_min          .300
_refine_diff_density_max         .32
_refine_diff_density_min         -.31
_refine_ls_abs_structure_details 'Flack (1983), 1016 Friedel pairs'
_refine_ls_abs_structure_Flack   -.03(3)
_refine_ls_extinction_coef       .0230
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1018
_refine_ls_R_factor_gt           .0194
_refine_ls_shift/su_max          .0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0370P)²+0.1736P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0573
_reflns_number_gt                991
_reflns_number_total             1018
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6112.cif
_cod_data_source_block           I
_cod_original_cell_volume        736.3(4)
_cod_database_code               2200917
_cod_database_fobs_code          2200917
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,z
1/2+x,1/2-y,-z
1/2-x,1/2+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
_atom_site_type_symbol
Ni1 .5000 .5000 .24618(6) .01720(10) Uani d S 1.00 . . Ni
O1 .14670(10) .52990(10) -.0244(3) .0304(4) Uani d . 1.00 . . O
O2 .34800(10) .4851(2) -.0009(3) .0230(5) Uani d . 1.00 . . O
O3 .3492(2) .4831(2) .4923(3) .0224(5) Uani d . 1.00 . . O
N1 .4786(2) .81260(10) .1327(4) .0352(5) Uani d . 1.00 . . N
N3 .4655(2) .65310(10) .2406(4) .0241(3) Uani d . 1.00 . . N
C2 .5369(2) .7229(2) .1337(5) .0302(5) Uani d . 1.00 . . C
C4 .3546(2) .70100(10) .3110(4) .0242(4) Uani d . 1.00 . . C
C5 .3630(2) .79980(10) .2441(6) .0324(4) Uani d . 1.00 . . C
C6 .2495(2) .6477(2) .4439(4) .0271(4) Uani d . 1.00 . . C
C7 .2436(2) .5347(2) .3873(4) .0214(4) Uani d . 1.00 . . C
C8 .2440(2) .51530(10) .0974(4) .0199(4) Uani d . 1.00 . . C
H1 .5056 .8719 .0817 .0332 Uiso calc . 1.00 . . H
H2 .6190 .7132 .0621 .0332 Uiso calc . 1.00 . . H
H3 .2991 .8565 .2722 .0332 Uiso calc . 1.00 . . H
H4 .2550 .6521 .6163 .0332 Uiso calc . 1.00 . . H
H5 .1724 .6830 .3980 .0332 Uiso calc . 1.00 . . H
H6 .1621 .5118 .4525 .0332 Uiso calc . 1.00 . . H
H7 .3586 .4886 .6334 .0332 Uiso calc . 1.00 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .003 .002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H .000 .000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N .006 .003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O .011 .006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Ni Ni .339 1.112
;International Tables for Crystallography
(1992, 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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 NI1 O2 1_555 2_665 103.28(8) no
O2 NI1 O3 1_555 1_555 76.78(6) yes
O2 NI1 O3 1_555 2_665 179.22(10) no
O2 NI1 N3 1_555 1_555 86.96(8) yes
O2 NI1 N3 1_555 2_665 92.04(9) no
O2 NI1 O3 2_665 1_555 76.77(6) no
O2 NI1 O3 2_665 2_665 179.22(10) no
O2 NI1 N3 2_665 1_555 86.96(9) no
O2 NI1 N3 2_665 2_665 92.04(9) no
O3 NI1 O3 1_555 2_665 103.17(9) no
O3 NI1 N3 1_555 1_555 88.71(7) yes
O3 NI1 N3 1_555 2_665 92.29(7) no
O3 NI1 N3 2_665 1_555 88.74(9) no
O3 NI1 N3 2_665 2_665 92.27(9) no
N3 NI1 N3 1_555 2_665 178.40(10) no
NI1 O2 C8 1_555 1_555 113.20(10) yes
NI1 O3 C7 1_555 1_555 108.70(10) yes
NI1 O3 H7 1_555 1_555 119.9 no
C7 O3 H7 1_555 1_555 115.9 no
C2 N1 C5 1_555 1_555 107.6(2) yes
C2 N1 H1 1_555 1_555 130.2 no
C5 N1 H1 1_555 1_555 122.2 no
NI1 N3 C2 1_555 1_555 126.40(10) yes
NI1 N3 C4 1_555 1_555 126.70(10) yes
C2 N3 C4 1_555 1_555 106.1(2) yes
N1 C2 N3 1_555 1_555 111.0(2) yes
N1 C2 H2 1_555 1_555 122.6 no
N3 C2 H2 1_555 1_555 126.4 no
N3 C4 C5 1_555 1_555 108.6(2) yes
N3 C4 C6 1_555 1_555 122.8(2) yes
C5 C4 C6 1_555 1_555 128.7(2) yes
N1 C5 C4 1_555 1_555 106.7(2) yes
N1 C5 H3 1_555 1_555 124.3 no
C4 C5 H3 1_555 1_555 128.9 no
C4 C6 C7 1_555 1_555 113.9(2) yes
C4 C6 H4 1_555 1_555 112.6 no
C4 C6 H5 1_555 1_555 106.7 no
C7 C6 H4 1_555 1_555 104.9 no
C7 C6 H5 1_555 1_555 113.0 no
H4 C6 H5 1_555 1_555 105.6 no
O3 C7 C6 1_555 1_555 111.4(2) yes
O3 C7 C8 1_555 1_555 107.2(2) yes
O3 C7 H6 1_555 1_555 114.4 no
C6 C7 C8 1_555 1_555 110.8(2) yes
C6 C7 H6 1_555 1_555 106.0 no
C8 C7 H6 1_555 1_555 107.0 no
O1 C8 O2 1_555 1_555 124.6(2) yes
O1 C8 C7 1_555 1_555 118.7(2) yes
O2 C8 C7 1_555 1_555 116.6(2) yes
N1 H1 N1 1_555 2_675 152.5 no
N1 H1 O3 1_555 4_556 82.8 no
N1 H1 O3 1_555 3_566 118.6 no
N1 H1 O3 2_675 4_556 61.92 no
N1 H1 O3 2_675 3_566 71.54 no
N1 H2 O3 1_555 2_665 116.5 no
N1 H2 O3 1_555 2_664 128.8 no
N1 H2 N1 1_555 3_565 144.3 no
N1 H2 O3 1_555 1_555 83.6 no
O3 H2 O3 2_665 2_664 89.0 no
O3 H2 N1 2_665 3_565 70.89 no
O3 H2 N1 2_664 3_565 54.14 no
O3 H2 O3 2_664 1_555 89.0 no
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
NI1 O2 . . 2.076(2) yes
NI1 O3 . . 2.066(2) yes
NI1 N3 . . 2.067(2) yes
O1 C8 . . 1.229(3) yes
O2 C8 . . 1.283(3) yes
O3 C7 . . 1.425(3) yes
O3 H7 . . .746 no
N1 C2 . . 1.343(3) yes
N1 C5 . . 1.369(3) yes
N1 H1 . . .880 no
N3 C2 . . 1.322(3) yes
N3 C4 . . 1.388(3) yes
C2 H2 . . .957 no
C4 C5 . . 1.361(3) yes
C4 C6 . . 1.493(3) yes
C5 H3 . . 1.025 no
C6 C7 . . 1.531(3) yes
C6 H4 . . .903 no
C6 H5 . . .974 no
C7 C8 . . 1.533(3) yes
C7 H6 . . .980 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O1 N1 2.810(2) 3_465
O1 O1 3.219(3) 2_565
O1 N1 3.228(2) 4_545
O1 C7 3.237(3) 1_554
O1 C5 3.266(3) 4_545
O1 C6 3.367(3) 1_554
O1 O3 3.372(2) 1_554
O1 C2 3.531(3) 3_465
O2 O3 2.643(2) 1_554
O2 C7 3.442(3) 1_554
O2 C5 3.564(3) 4_545
O3 C8 3.375(2) 1_556
O3 C5 3.594(3) 4_546
C2 C6 3.593(3) 3_566
C5 C8 3.558(3) 4_555
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
N1 H1 O1 3_565 .88 2.01 2.808(3) 150 yes
O3 H7 O2 1_556 .75 1.91 2.642(2) 167 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
NI1 O2 C8 O1 1_555 1_555 1_555 1_555 167.0(2) no
NI1 O2 C8 C7 1_555 1_555 1_555 1_555 -12.6(2) no
NI1 O2 C8 O1 1_555 2_665 2_665 2_665 167.0(2) no
NI1 O2 C8 C7 1_555 2_665 2_665 2_665 -12.6(2) no
NI1 O3 C7 C6 1_555 1_555 1_555 1_555 -81.2(2) no
NI1 O3 C7 C8 1_555 1_555 1_555 1_555 40.2(2) no
NI1 O3 C7 C6 1_555 2_665 2_665 2_665 -81.2(2) no
NI1 O3 C7 C8 1_555 2_665 2_665 2_665 40.2(2) no
NI1 N3 C2 N1 1_555 1_555 1_555 1_555 171.1(2) no
NI1 N3 C4 C5 1_555 1_555 1_555 1_555 -171.0(2) no
NI1 N3 C4 C6 1_555 1_555 1_555 1_555 10.5(3) no
NI1 N3 C2 N1 1_555 2_665 2_665 2_665 171.1(2) no
NI1 N3 C4 C5 1_555 2_665 2_665 2_665 -171.0(2) no
NI1 N3 C4 C6 1_555 2_665 2_665 2_665 10.5(3) no
O1 C8 C7 O3 1_555 1_555 1_555 1_555 161.7(2) no
O1 C8 C7 C6 1_555 1_555 1_555 1_555 -76.5(2) no
O2 NI1 O2 C8 1_555 1_555 2_665 2_665 -153.1(2) no
O2 NI1 O3 C7 1_555 1_555 1_555 1_555 -37.40(10) no
O2 NI1 N3 C2 1_555 1_555 1_555 1_555 -110.7(2) no
O2 NI1 N3 C4 1_555 1_555 1_555 1_555 58.3(2) no
O2 NI1 N3 C2 1_555 1_555 2_665 2_665 -7.5(2) no
O2 NI1 N3 C4 1_555 1_555 2_665 2_665 161.5(2) no
O2 C8 C7 O3 1_555 1_555 1_555 1_555 -18.7(3) no
O2 C8 C7 C6 1_555 1_555 1_555 1_555 103.1(2) no
O3 NI1 O2 C8 1_555 1_555 1_555 1_555 27.6(2) no
O3 NI1 O3 C7 1_555 1_555 2_665 2_665 141.8(2) no
O3 NI1 N3 C2 1_555 1_555 1_555 1_555 172.5(2) no
O3 NI1 N3 C4 1_555 1_555 1_555 1_555 -18.6(2) no
O3 NI1 N3 C2 1_555 1_555 2_665 2_665 69.3(2) no
O3 NI1 N3 C4 1_555 1_555 2_665 2_665 -121.7(2) no
O3 C7 C6 C4 1_555 1_555 1_555 1_555 67.1(2) no
N1 C2 N3 C4 1_555 1_555 1_555 1_555 .3(3) no
N1 C5 C4 N3 1_555 1_555 1_555 1_555 .1(3) no
N1 C5 C4 C6 1_555 1_555 1_555 1_555 178.5(2) no
N3 NI1 O2 C8 1_555 1_555 1_555 1_555 -61.8(2) no
N3 NI1 O2 C8 1_555 1_555 2_665 2_665 119.5(2) no
N3 NI1 O3 C7 1_555 1_555 1_555 1_555 49.80(10) no
N3 NI1 O3 C7 1_555 1_555 2_665 2_665 -129.00(10) no
N3 C2 N1 C5 1_555 1_555 1_555 1_555 -.3(3) no
N3 C4 C6 C7 1_555 1_555 1_555 1_555 -27.1(3) no
C2 N1 C5 C4 1_555 1_555 1_555 1_555 .1(3) no
C2 N3 C4 C5 1_555 1_555 1_555 1_555 -.2(3) no
C2 N3 C4 C6 1_555 1_555 1_555 1_555 -178.8(2) no
C4 C6 C7 C8 1_555 1_555 1_555 1_555 -52.2(2) no
C5 C4 C6 C7 1_555 1_555 1_555 1_555 154.7(2) no
