#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2200917.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-(1<i>H</i>-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_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       \w-2\q
_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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0370P)^2^+0.1736P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0573
_reflns_number_gt                991
_reflns_number_total             1018
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    na6112.cif
_[local]_cod_data_source_block   I
_cod_original_cell_volume        736.3(4)
_cod_database_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_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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Ni1 .0180(2) .0183(2) .0154(2) .00250(10) .0000 .0000
O1 .0234(7) .0363(8) .0317(8) .0064(6) -.0050(7) .0005(7)
O2 .0204(6) .0330(10) .0160(6) .0053(8) -.0010(6) -.0007(7)
O3 .0244(6) .0270(10) .0155(6) .0033(8) .0013(6) .0038(6)
N1 .0370(10) .0201(8) .0480(10) -.0048(7) -.0001(10) .0051(8)
N3 .0244(7) .0193(7) .0287(8) .0016(6) .0015(8) .0010(8)
C2 .0270(9) .0249(10) .0390(10) -.0014(8) .0010(10) .0036(10)
C4 .0273(9) .0203(9) .0250(10) .0022(8) .0003(8) -.0021(8)
C5 .0350(10) .0203(8) .0420(10) .0032(7) .0010(10) -.0010(10)
C6 .0295(9) .0263(9) .0260(10) .0071(9) .0083(9) -.0033(8)
C7 .0196(8) .0241(9) .0204(9) .0009(8) .0041(8) .0026(7)
C8 .0238(9) .0169(10) .0191(8) .0004(8) .0004(8) .0028(7)
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_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