#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/10/01/1100159.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1100159
loop_
_publ_author_name
'Carballo, Rosa'
'Vazquez-Lopez, Ezequiel M.'
'Covelo, Berta'
'Garcia-Martinez, Emilia'
'Castineiras, Alfonso'
'Niclos, Juan'
_publ_section_title
;
 'Solid state coordination chemistry of mononuclear
  mixed-ligand complexes of Ni(II), Cu(II) and Zn(II)
  with α-hydroxycarboxylic acids and imidazole'
;
_journal_name_full               Polyhedron
_journal_page_first              1505
_journal_page_last               1518
_journal_paper_doi               10.1016/j.poly.2004.02.028
_journal_volume                  23
_journal_year                    2004
_chemical_formula_sum            'C9 H14 Cu N2 O6'
_chemical_formula_weight         309.76
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 92.324(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.422(3)
_cell_length_b                   13.436(7)
_cell_length_c                   17.000(9)
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_cell_volume                     1237.4(11)
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.908
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0864
_diffrn_reflns_av_sigmaI/netI    0.2921
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6303
_diffrn_reflns_theta_full        27.98
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_exptl_absorpt_coefficient_mu    1.786
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.753
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2705
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.754
_refine_ls_R_factor_all          0.2235
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0199P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0926
_reflns_number_gt                902
_reflns_number_total             2705
_reflns_threshold_expression     >2sigma(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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' 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:

'_atom_sites_solution_hydrogens' value 'geom & difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1100159
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.34092(13) 0.24814(7) 0.02425(5) 0.0369(2) Uani 1 1 d . . .
O11 O 0.6121(7) 0.1625(3) -0.0060(3) 0.0345(12) Uani 1 1 d . . .
O12 O 0.7480(7) 0.0344(3) -0.0724(3) 0.0491(14) Uani 1 1 d . . .
O13 O 0.1610(8) 0.1502(3) -0.0718(3) 0.0476(13) Uani 1 1 d D . .
C11 C 0.5812(12) 0.0944(4) -0.0576(4) 0.0330(19) Uani 1 1 d . . .
C12 C 0.3363(12) 0.0829(5) -0.1015(5) 0.045(2) Uani 1 1 d . . .
H12 H 0.2768 0.0146 -0.0950 0.053 Uiso 1 1 calc R . .
C13 C 0.3702(14) 0.1024(6) -0.1871(4) 0.098(3) Uani 1 1 d . . .
H13A H 0.2164 0.0922 -0.2160 0.147 Uiso 1 1 calc R . .
H13B H 0.4920 0.0576 -0.2063 0.147 Uiso 1 1 calc R . .
H13C H 0.4239 0.1698 -0.1940 0.147 Uiso 1 1 calc R . .
O21 O 0.0853(8) 0.3252(3) 0.0701(3) 0.0450(13) Uani 1 1 d . . .
O22 O -0.2260(9) 0.3179(3) 0.1507(3) 0.0760(18) Uani 1 1 d . . .
O23 O 0.2597(8) 0.1564(3) 0.1098(3) 0.0423(13) Uani 1 1 d D . .
C21 C -0.0436(13) 0.2834(4) 0.1211(4) 0.041(2) Uani 1 1 d . . .
C22 C 0.0287(12) 0.1764(4) 0.1431(4) 0.041(2) Uani 1 1 d . . .
H22 H -0.0946 0.1313 0.1189 0.050 Uiso 1 1 calc R . .
C23 C 0.0388(15) 0.1589(5) 0.2283(4) 0.091(3) Uani 1 1 d . . .
H23A H 0.0740 0.0900 0.2386 0.137 Uiso 1 1 calc R . .
H23B H -0.1171 0.1759 0.2494 0.137 Uiso 1 1 calc R . .
H23C H 0.1663 0.1993 0.2527 0.137 Uiso 1 1 calc R . .
N1 N 0.4281(9) 0.3568(3) -0.0448(3) 0.0325(14) Uani 1 1 d . . .
N2 N 0.4027(10) 0.4991(4) -0.1093(3) 0.0352(14) Uani 1 1 d . . .
C1 C 0.2965(11) 0.4378(5) -0.0603(4) 0.037(2) Uani 1 1 d . . .
H1 H 0.1445 0.4503 -0.0389 0.045 Uiso 1 1 calc R . .
C2 C 0.6379(12) 0.3676(4) -0.0881(4) 0.041(2) Uani 1 1 d . . .
H2 H 0.7668 0.3221 -0.0903 0.049 Uiso 1 1 calc R . .
C3 C 0.6228(12) 0.4556(5) -0.1265(4) 0.045(2) Uani 1 1 d . . .
H3 H 0.7408 0.4820 -0.1588 0.054 Uiso 1 1 calc R . .
H13 H 0.034(7) 0.121(4) -0.060(4) 0.08(3) Uiso 1 1 d D . .
H23 H 0.294(9) 0.1013(18) 0.100(3) 0.026(19) Uiso 1 1 d D . .
H20 H 0.3002 0.5557 -0.1281 0.69(17) Uiso 1 1 d . . .
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'
Cu Cu 0.3201 1.2651 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O21 Cu N1 92.14(19) . . ?
O21 Cu O11 171.22(19) . . ?
N1 Cu O11 94.56(18) . . ?
O21 Cu O23 81.44(18) . . ?
N1 Cu O23 169.4(2) . . ?
O11 Cu O23 91.08(17) . . ?
O21 Cu O13 107.83(18) . . ?
N1 Cu O13 96.2(2) . . ?
O11 Cu O13 77.09(17) . . ?
O23 Cu O13 93.8(2) . . ?
C11 O11 Cu 121.7(4) . . ?
C12 O13 Cu 110.4(4) . . ?
O12 C11 O11 121.8(6) . . ?
O12 C11 C12 117.9(6) . . ?
O11 C11 C12 120.3(6) . . ?
O13 C12 C13 110.2(6) . . ?
O13 C12 C11 110.4(6) . . ?
C13 C12 C11 108.9(6) . . ?
C21 O21 Cu 117.7(4) . . ?
C22 O23 Cu 113.8(4) . . ?
O22 C21 O21 126.3(6) . . ?
O22 C21 C22 117.4(6) . . ?
O21 C21 C22 116.1(6) . . ?
O23 C22 C23 111.4(6) . . ?
O23 C22 C21 107.5(5) . . ?
C23 C22 C21 112.9(6) . . ?
C1 N1 C2 104.8(5) . . ?
C1 N1 Cu 126.6(4) . . ?
C2 N1 Cu 128.6(4) . . ?
C1 N2 C3 106.0(5) . . ?
N2 C1 N1 113.1(6) . . ?
C3 C2 N1 108.2(6) . . ?
C2 C3 N2 107.8(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu O21 1.920(4) . ?
Cu N1 1.944(5) . ?
Cu O11 1.952(4) . ?
Cu O23 1.969(4) . ?
Cu O13 2.284(5) . ?
O11 C11 1.274(7) . ?
O12 C11 1.244(7) . ?
O13 C12 1.420(7) . ?
C11 C12 1.505(8) . ?
C12 C13 1.498(9) . ?
O21 C21 1.268(7) . ?
O22 C21 1.220(7) . ?
O23 C22 1.421(7) . ?
C21 C22 1.532(7) . ?
C22 C23 1.466(8) . ?
N1 C1 1.322(6) . ?
N1 C2 1.387(7) . ?
N2 C1 1.320(6) . ?
N2 C3 1.370(7) . ?
C2 C3 1.352(8) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O13 H13 O12 0.823(19) 1.94(3) 2.727(6) 159(7) 1_455
O13 H13 O11 0.823(19) 2.56(4) 3.226(6) 138(6) 1_455
O23 H23 O12 0.781(19) 1.90(3) 2.642(6) 160(5) 3_655
N2 H20 O22 0.988(5) 1.783(4) 2.721(7) 157.3(3) 3_565
C1 H1 O21 0.93 2.53 2.953(8) 107.9 .
