#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/27/2202755.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_2202755
loop_
_publ_author_name
'Zhi Min Jin'
'Lin He'
'Liang Shen'
'Mei Chao Li'
'Mao Lin Hu'
_publ_section_title
Tris(1H-imidazole-κN³)(<small>DL</small>-malato-κ³O,O',O'')cobalt(II)
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1053
_journal_page_last               m1055
_journal_paper_doi               10.1107/S1600536803023407
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          '[Co (C4 H4 O5) (C3 H4 N2)3]'
_chemical_formula_moiety         'C13 H16 Co N6 O5'
_chemical_formula_sum            'C13 H16 Co N6 O5'
_chemical_formula_weight         395.25
_chemical_name_systematic
;
Tris(1H-imidazole-\kN³)(dl-malate-κ³O,O',O'')cobalt(II)
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.710(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4820(10)
_cell_length_b                   8.5970(10)
_cell_length_c                   22.489(4)
_cell_measurement_reflns_used    29
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15.71
_cell_measurement_theta_min      2.99
_cell_volume                     1639.8(4)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'SHELXTL (Siemens, 1996)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0117
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3099
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        1.35
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.085
_exptl_absorpt_correction_T_max  0.620
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.313
_refine_ls_extinction_coef       0.0066(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0356
_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)+(0.0440P)²+1.2283P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0953
_reflns_number_gt                2392
_reflns_number_total             2890
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6259.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2202755
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_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
Co -0.32679(4) 0.26070(4) -0.374365(15) 0.02972(15) Uani d . 1 . . Co
O1 -0.4083(2) 0.4938(2) -0.36153(8) 0.0364(5) Uani d . 1 . . O
O2 -0.5402(4) 0.6662(4) -0.31193(11) 0.0749(9) Uani d . 1 . . O
O3 -0.3090(3) 0.2573(3) -0.28027(9) 0.0466(6) Uani d . 1 . . O
O4 -0.1014(2) 0.3521(2) -0.35443(9) 0.0389(5) Uani d . 1 . . O
O5 -0.0058(3) 0.5411(3) -0.29756(11) 0.0570(7) Uani d . 1 . . O
N1 -0.2348(3) 0.0327(3) -0.37980(11) 0.0386(6) Uani d . 1 . . N
N2 -0.1311(3) -0.1897(3) -0.35282(14) 0.0506(7) Uani d . 1 . . N
H2' -0.0869 -0.2597 -0.3310 0.061 Uiso calc R 1 . . H
N3 -0.3062(3) 0.3045(3) -0.46586(10) 0.0367(6) Uani d . 1 . . N
N4 -0.3671(4) 0.3573(4) -0.55806(13) 0.0670(10) Uani d . 1 . . N
H4' -0.4234 0.3715 -0.5896 0.080 Uiso calc R 1 . . H
N5 -0.5661(3) 0.1887(3) -0.38167(10) 0.0350(6) Uani d . 1 . . N
N6 -0.8238(3) 0.2014(4) -0.38020(12) 0.0463(7) Uani d . 1 . . N
H6' -0.9172 0.2379 -0.3753 0.056 Uiso calc R 1 . . H
C1 -0.4363(3) 0.5630(4) -0.31380(13) 0.0361(7) Uani d . 1 . . C
C2 -0.3474(4) 0.5249(5) -0.25758(14) 0.0505(9) Uani d . 1 . . C
H2A -0.2946 0.6183 -0.2437 0.061 Uiso calc R 1 . . H
H2B -0.4229 0.4952 -0.2276 0.061 Uiso calc R 1 . . H
C3 -0.2283(4) 0.3990(4) -0.26248(13) 0.0448(8) Uani d . 1 . . C
H3 -0.1784 0.3827 -0.2234 0.054 Uiso calc R 1 . . H
C4 -0.0994(3) 0.4358(4) -0.30816(13) 0.0369(7) Uani d . 1 . . C
C5 -0.2366(4) -0.0666(4) -0.42733(15) 0.0468(8) Uani d . 1 . . C
H5 -0.2746 -0.0426 -0.4652 0.056 Uiso calc R 1 . . H
C6 -0.1741(4) -0.2057(4) -0.41069(17) 0.0542(9) Uani d . 1 . . C
H6 -0.1630 -0.2938 -0.4342 0.065 Uiso calc R 1 . . H
C7 -0.1696(4) -0.0455(4) -0.33554(15) 0.0439(8) Uani d . 1 . . C
H7 -0.1526 -0.0061 -0.2975 0.053 Uiso calc R 1 . . H
C8 -0.1731(4) 0.3384(6) -0.49678(16) 0.0737(13) Uani d . 1 . . C
H8 -0.0715 0.3395 -0.4808 0.088 Uiso calc R 1 . . H
C9 -0.2109(5) 0.3701(5) -0.55384(16) 0.0718(13) Uani d . 1 . . C
H9 -0.1419 0.3957 -0.5841 0.086 Uiso calc R 1 . . H
C10 -0.4202(4) 0.3187(4) -0.50478(15) 0.0535(9) Uani d . 1 . . C
H10 -0.5261 0.3035 -0.4963 0.064 Uiso calc R 1 . . H
C11 -0.6281(4) 0.0517(4) -0.40156(15) 0.0472(8) Uani d . 1 . . C
H11 -0.5693 -0.0335 -0.4138 0.057 Uiso calc R 1 . . H
C12 -0.7875(4) 0.0577(5) -0.40085(15) 0.0525(9) Uani d . 1 . . C
H12 -0.8576 -0.0204 -0.4122 0.063 Uiso calc R 1 . . H
C13 -0.6895(3) 0.2756(4) -0.36887(13) 0.0414(8) Uani d . 1 . . C
H13 -0.6831 0.3762 -0.3538 0.050 Uiso calc R 1 . . H
H3O -0.407(5) 0.288(5) -0.2750(19) 0.080 Uiso d . 1 . . H
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'
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
_geom_angle_publ_flag
N3 Co O4 93.18(9) yes
N3 Co N1 94.26(10) yes
O4 Co N1 91.33(9) yes
N3 Co O3 166.98(9) ?
O4 Co O3 74.92(9) yes
N1 Co O3 91.33(9) yes
N3 Co N5 93.85(9) yes
O4 Co N5 170.50(9) ?
N1 Co N5 94.50(10) yes
O3 Co N5 97.43(9) yes
N3 Co O1 89.73(8) yes
O4 Co O1 85.21(8) yes
N1 Co O1 174.87(8) ?
O3 Co O1 84.11(8) yes
N5 Co O1 88.45(9) yes
C1 O1 Co 128.69(19) ?
C3 O3 Co 106.93(17) ?
C3 O3 H3O 99(3) ?
Co O3 H3O 94(3) ?
C4 O4 Co 112.92(18) ?
C7 N1 C5 105.8(3) ?
C7 N1 Co 125.6(2) ?
C5 N1 Co 128.6(2) ?
C7 N2 C6 108.0(3) ?
C7 N2 H2' 126.0 ?
C6 N2 H2' 126.0 ?
C10 N3 C8 104.4(3) ?
C10 N3 Co 127.3(2) ?
C8 N3 Co 128.1(2) ?
C10 N4 C9 107.7(3) ?
C10 N4 H4' 126.1 ?
C9 N4 H4' 126.1 ?
C13 N5 C11 104.9(3) ?
C13 N5 Co 125.2(2) ?
C11 N5 Co 129.8(2) ?
C13 N6 C12 107.8(3) ?
C13 N6 H6' 126.1 ?
C12 N6 H6' 126.1 ?
O2 C1 O1 120.4(3) ?
O2 C1 C2 118.3(3) ?
O1 C1 C2 121.3(3) ?
C3 C2 C1 115.6(3) ?
C3 C2 H2A 108.4 ?
C1 C2 H2A 108.4 ?
C3 C2 H2B 108.4 ?
C1 C2 H2B 108.4 ?
H2A C2 H2B 107.4 ?
O3 C3 C2 108.2(3) ?
O3 C3 C4 108.9(2) ?
C2 C3 C4 112.9(3) ?
O3 C3 H3 108.9 ?
C2 C3 H3 108.9 ?
C4 C3 H3 108.9 ?
O5 C4 O4 125.6(3) ?
O5 C4 C3 119.0(3) ?
O4 C4 C3 115.4(3) ?
C6 C5 N1 109.5(3) ?
C6 C5 H5 125.3 ?
N1 C5 H5 125.3 ?
N2 C6 C5 106.0(3) ?
N2 C6 H6 127.0 ?
C5 C6 H6 127.0 ?
N1 C7 N2 110.8(3) ?
N1 C7 H7 124.6 ?
N2 C7 H7 124.6 ?
C9 C8 N3 109.9(3) ?
C9 C8 H8 125.1 ?
N3 C8 H8 125.1 ?
N4 C9 C8 106.0(3) ?
N4 C9 H9 127.0 ?
C8 C9 H9 127.0 ?
N3 C10 N4 111.9(3) ?
N3 C10 H10 124.0 ?
N4 C10 H10 124.0 ?
C12 C11 N5 110.1(3) ?
C12 C11 H11 124.9 ?
N5 C11 H11 124.9 ?
C11 C12 N6 105.7(3) ?
C11 C12 H12 127.2 ?
N6 C12 H12 127.2 ?
N5 C13 N6 111.5(3) ?
N5 C13 H13 124.2 ?
N6 C13 H13 124.2 ?
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
Co N3 . 2.101(2) yes
Co O4 . 2.110(2) yes
Co N1 . 2.114(3) yes
Co O3 . 2.120(2) yes
Co N5 . 2.127(2) yes
Co O1 . 2.141(2) yes
O1 C1 . 1.252(3) yes
O2 C1 . 1.252(4) yes
O3 C3 . 1.451(4) yes
O3 H3O . 0.88(4) ?
O4 C4 . 1.265(4) yes
O5 C4 . 1.225(4) yes
N1 C7 . 1.317(4) yes
N1 C5 . 1.368(4) ?
N2 C7 . 1.340(4) ?
N2 C6 . 1.354(5) ?
N2 H2' . 0.8600 ?
N3 C10 . 1.302(4) yes
N3 C8 . 1.365(4) ?
N4 C10 . 1.327(5) ?
N4 C9 . 1.332(5) ?
N4 H4' . 0.8600 ?
N5 C13 . 1.321(4) yes
N5 C11 . 1.363(4) ?
N6 C13 . 1.327(4) ?
N6 C12 . 1.357(5) ?
N6 H6' . 0.8600 ?
C1 C2 . 1.500(4) ?
C2 C3 . 1.485(5) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.543(4) ?
C3 H3 . 0.9800 ?
C5 C6 . 1.358(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.346(5) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.354(5) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 H13 . 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
C2 H2A O5 . 0.97 2.82 3.047(4) 94 ?
C5 H5 N3 . 0.93 3.00 3.356(4) 105 ?
C7 H7 O3 . 0.93 2.66 3.124(4) 112 ?
C8 H8 O4 . 0.93 2.86 3.253(4) 107 ?
C10 H10 N5 . 0.93 2.78 3.245(4) 112 ?
C11 H11 N1 . 0.93 2.98 3.369(4) 107 ?
C13 H13 O1 . 0.93 2.55 3.037(4) 113 ?
C13 H13 O2 . 0.93 2.92 3.805(5) 159 ?
N2 H2' O5 1_545 0.86 1.99 2.828(4) 165 yes
N4 H4' O1 3_464 0.86 2.13 2.907(4) 150 yes
N4 H4' O2 3_464 0.86 2.25 3.025(4) 149 yes
N6 H6' O4 1_455 0.86 1.91 2.755(3) 168 yes
C2 H2B O2 2_444 0.97 2.98 3.591(5) 122 ?
O3 H3O O2 2_444 0.88(4) 2.27(4) 2.572(3) 100(3) yes
C2 H2B N5 2_454 0.97 2.97 3.519(4) 117 ?
C7 H7 O5 2_544 0.93 2.54 3.409(4) 155 ?
C11 H11 N4 3_454 0.93 2.90 3.631(5) 136 ?
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
N3 Co O1 C1 -173.9(2)
O4 Co O1 C1 -80.7(2)
N1 Co O1 C1 -33.0(11)
O3 Co O1 C1 -5.4(2)
N5 Co O1 C1 92.3(2)
N3 Co O3 C3 14.5(5)
O4 Co O3 C3 38.95(18)
N1 Co O3 C3 129.97(19)
N5 Co O3 C3 -135.31(19)
O1 Co O3 C3 -47.65(19)
N3 Co O4 C4 137.8(2)
N1 Co O4 C4 -127.9(2)
O3 Co O4 C4 -36.8(2)
N5 Co O4 C4 0.1(6)
O1 Co O4 C4 48.3(2)
N3 Co N1 C7 157.4(3)
O4 Co N1 C7 64.1(3)
O3 Co N1 C7 -10.8(3)
N5 Co N1 C7 -108.4(3)
O1 Co N1 C7 16.6(11)
N3 Co N1 C5 -26.2(3)
O4 Co N1 C5 -119.5(3)
O3 Co N1 C5 165.5(3)
N5 Co N1 C5 68.0(3)
O1 Co N1 C5 -167.0(9)
O4 Co N3 C10 -158.2(3)
N1 Co N3 C10 110.2(3)
O3 Co N3 C10 -134.6(4)
N5 Co N3 C10 15.4(3)
O1 Co N3 C10 -73.0(3)
O4 Co N3 C8 15.2(3)
N1 Co N3 C8 -76.3(3)
O3 Co N3 C8 38.8(6)
N5 Co N3 C8 -171.2(3)
O1 Co N3 C8 100.4(3)
N3 Co N5 C13 -100.5(2)
O4 Co N5 C13 37.1(7)
N1 Co N5 C13 164.9(2)
O3 Co N5 C13 72.9(2)
O1 Co N5 C13 -10.9(2)
N3 Co N5 C11 76.9(3)
O4 Co N5 C11 -145.4(5)
N1 Co N5 C11 -17.6(3)
O3 Co N5 C11 -109.6(3)
O1 Co N5 C11 166.6(3)
Co O1 C1 O2 -149.6(3)
Co O1 C1 C2 30.2(4)
O2 C1 C2 C3 178.7(3)
O1 C1 C2 C3 -1.1(5)
Co O3 C3 C2 85.8(2)
Co O3 C3 C4 -37.3(3)
C1 C2 C3 O3 -61.1(4)
C1 C2 C3 C4 59.6(4)
Co O4 C4 O5 -153.9(2)
Co O4 C4 C3 25.7(3)
O3 C3 C4 O5 -171.7(3)
C2 C3 C4 O5 68.0(4)
O3 C3 C4 O4 8.6(3)
C2 C3 C4 O4 -111.6(3)
C7 N1 C5 C6 1.0(4)
Co N1 C5 C6 -175.9(2)
C7 N2 C6 C5 0.9(4)
N1 C5 C6 N2 -1.2(4)
C5 N1 C7 N2 -0.4(4)
Co N1 C7 N2 176.7(2)
C6 N2 C7 N1 -0.3(4)
C10 N3 C8 C9 -0.8(5)
Co N3 C8 C9 -175.4(3)
C10 N4 C9 C8 -0.1(5)
N3 C8 C9 N4 0.6(6)
C8 N3 C10 N4 0.8(4)
Co N3 C10 N4 175.4(2)
C9 N4 C10 N3 -0.4(5)
C13 N5 C11 C12 0.3(4)
Co N5 C11 C12 -177.5(2)
N5 C11 C12 N6 0.1(4)
C13 N6 C12 C11 -0.5(4)
C11 N5 C13 N6 -0.7(3)
Co N5 C13 N6 177.34(19)
C12 N6 C13 N5 0.7(4)
