#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/10/01/1100156.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_1100156
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            'C22 H22 N4 Ni O6'
_chemical_formula_weight         497.15
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                106.910(7)
_cell_angle_beta                 110.208(6)
_cell_angle_gamma                90.172(7)
_cell_formula_units_Z            2
_cell_length_a                   9.170(3)
_cell_length_b                   10.936(3)
_cell_length_c                   12.717(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1137.4(6)
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.800
_diffrn_measured_fraction_theta_max 0.800
_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  0.0628
_diffrn_reflns_av_sigmaI/netI    0.3102
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6291
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7469
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.644
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4405
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.644
_refine_ls_R_factor_all          0.1784
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0816
_reflns_number_gt                1452
_reflns_number_total             4405
_reflns_threshold_expression     >2sigma(I)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1100156
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.24243(9) 0.24080(8) 0.49120(7) 0.0389(2) Uani 1 d . . .
O11 O 0.2049(4) 0.4045(3) 0.4461(3) 0.0397(10) Uani 1 d . . .
O12 O 0.0315(4) 0.5157(3) 0.3550(3) 0.0437(10) Uani 1 d . . .
O13 O 0.0133(4) 0.1985(4) 0.3616(3) 0.0392(10) Uani 1 d D . .
C11 C 0.0692(6) 0.4201(5) 0.3883(4) 0.0309(14) Uani 1 d . . .
C12 C -0.0612(5) 0.3098(5) 0.3567(4) 0.0316(14) Uani 1 d . . .
H12 H -0.1047 0.3312 0.4193 0.038 Uiso 1 calc R . .
C13 C -0.1945(6) 0.2945(5) 0.2417(5) 0.0359(14) Uani 1 d . . .
C14 C -0.2053(7) 0.2016(7) 0.1414(6) 0.071(2) Uani 1 d . . .
H14 H -0.1325 0.1425 0.1421 0.085 Uiso 1 calc R . .
C15 C -0.3274(8) 0.1955(8) 0.0368(6) 0.095(3) Uani 1 d . . .
H15 H -0.3336 0.1324 -0.0324 0.114 Uiso 1 calc R . .
C16 C -0.4360(9) 0.2774(8) 0.0326(6) 0.090(3) Uani 1 d . . .
H16 H -0.5164 0.2715 -0.0381 0.108 Uiso 1 calc R . .
C17 C -0.4262(7) 0.3686(7) 0.1332(8) 0.085(3) Uani 1 d . . .
H17 H -0.5015 0.4256 0.1317 0.102 Uiso 1 calc R . .
C18 C -0.3064(7) 0.3790(6) 0.2385(5) 0.0592(18) Uani 1 d . . .
H18 H -0.3012 0.4426 0.3071 0.071 Uiso 1 calc R . .
O21 O 0.2420(4) 0.0809(3) 0.5412(3) 0.0419(11) Uani 1 d . . .
O22 O 0.1827(4) -0.0106(3) 0.6587(3) 0.0453(11) Uani 1 d . . .
O23 O 0.1401(4) 0.2943(4) 0.6207(3) 0.0437(11) Uani 1 d D . .
C21 C 0.1770(5) 0.0777(5) 0.6120(5) 0.0334(15) Uani 1 d . . .
C22 C 0.0817(5) 0.1882(5) 0.6429(4) 0.0334(14) Uani 1 d . . .
H22 H -0.0263 0.1619 0.5873 0.040 Uiso 1 calc R . .
C23 C 0.0774(6) 0.2226(6) 0.7649(5) 0.0370(15) Uani 1 d . . .
C24 C -0.0007(7) 0.1388(6) 0.7953(6) 0.074(2) Uani 1 d . . .
H24 H -0.0502 0.0607 0.7391 0.089 Uiso 1 calc R . .
C25 C -0.0084(10) 0.1670(9) 0.9077(9) 0.104(3) Uani 1 d . . .
H25 H -0.0631 0.1096 0.9261 0.125 Uiso 1 calc R . .
C26 C 0.0653(11) 0.2791(10) 0.9881(8) 0.111(4) Uani 1 d . . .
H26 H 0.0640 0.2972 1.0639 0.133 Uiso 1 calc R . .
C27 C 0.1425(8) 0.3682(8) 0.9635(7) 0.096(3) Uani 1 d . . .
H27 H 0.1875 0.4476 1.0194 0.115 Uiso 1 calc R . .
C28 C 0.1512(6) 0.3349(7) 0.8498(6) 0.063(2) Uani 1 d . . .
H28 H 0.2090 0.3913 0.8327 0.076 Uiso 1 calc R . .
N1 N 0.3350(5) 0.1609(4) 0.3662(4) 0.0430(13) Uani 1 d . . .
N2 N 0.5156(6) 0.0886(5) 0.2955(5) 0.0640(16) Uani 1 d . . .
H20 H 0.5979 0.0542 0.2897 0.077 Uiso 1 calc R . .
C1 C 0.4677(7) 0.1082(6) 0.3846(6) 0.0576(19) Uani 1 d . . .
H1 H 0.5209 0.0875 0.4528 0.069 Uiso 1 calc R . .
C3 C 0.4101(8) 0.1331(7) 0.2142(6) 0.078(2) Uani 1 d . . .
H3 H 0.4138 0.1340 0.1422 0.093 Uiso 1 calc R . .
C2 C 0.2997(6) 0.1757(6) 0.2582(5) 0.0600(19) Uani 1 d . . .
H2 H 0.2119 0.2103 0.2202 0.072 Uiso 1 calc R . .
N3 N 0.4590(5) 0.3143(4) 0.6127(4) 0.0423(14) Uani 1 d . . .
N4 N 0.7074(5) 0.3904(4) 0.6804(5) 0.0563(15) Uani 1 d . . .
H40 H 0.7919 0.4287 0.6843 0.068 Uiso 1 calc R . .
C4 C 0.5678(7) 0.3752(6) 0.5969(5) 0.0594(19) Uani 1 d . . .
H4 H 0.5492 0.4055 0.5327 0.071 Uiso 1 calc R . .
C6 C 0.6927(7) 0.3346(6) 0.7584(5) 0.064(2) Uani 1 d . . .
H6 H 0.7707 0.3283 0.8259 0.076 Uiso 1 calc R . .
C5 C 0.5375(7) 0.2894(6) 0.7158(5) 0.0544(18) Uani 1 d . . .
H5 H 0.4913 0.2473 0.7522 0.065 Uiso 1 calc R . .
H23 H 0.076(5) 0.356(4) 0.630(5) 0.08(2) Uiso 1 d D . .
H13 H -0.037(5) 0.135(4) 0.369(5) 0.07(2) Uiso 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Ni Ni 0.3393 1.1124 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
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 Ni O11 169.40(14) . . ?
O21 Ni N3 93.05(18) . . ?
O11 Ni N3 93.24(17) . . ?
O21 Ni N1 94.40(17) . . ?
O11 Ni N1 94.03(17) . . ?
N3 Ni N1 90.92(18) . . ?
O21 Ni O23 77.03(15) . . ?
O11 Ni O23 94.26(15) . . ?
N3 Ni O23 91.71(18) . . ?
N1 Ni O23 171.15(18) . . ?
O21 Ni O13 97.12(14) . . ?
O11 Ni O13 76.31(14) . . ?
N3 Ni O13 169.49(18) . . ?
N1 Ni O13 90.90(17) . . ?
O23 Ni O13 88.04(15) . . ?
C11 O11 Ni 119.3(3) . . ?
C12 O13 Ni 112.1(3) . . ?
O12 C11 O11 125.3(5) . . ?
O12 C11 C12 118.5(5) . . ?
O11 C11 C12 116.2(5) . . ?
O13 C12 C13 114.2(4) . . ?
O13 C12 C11 106.7(4) . . ?
C13 C12 C11 113.5(4) . . ?
C14 C13 C18 119.2(6) . . ?
C14 C13 C12 121.6(6) . . ?
C18 C13 C12 119.2(5) . . ?
C13 C14 C15 119.1(7) . . ?
C16 C15 C14 122.2(8) . . ?
C15 C16 C17 118.6(8) . . ?
C16 C17 C18 121.1(8) . . ?
C17 C18 C13 119.8(6) . . ?
C21 O21 Ni 119.1(3) . . ?
C22 O23 Ni 113.5(3) . . ?
O21 C21 O22 124.8(5) . . ?
O21 C21 C22 117.2(5) . . ?
O22 C21 C22 117.9(5) . . ?
O23 C22 C23 112.3(5) . . ?
O23 C22 C21 107.0(4) . . ?
C23 C22 C21 115.3(4) . . ?
C28 C23 C24 117.4(6) . . ?
C28 C23 C22 122.2(6) . . ?
C24 C23 C22 120.4(6) . . ?
C23 C24 C25 122.4(7) . . ?
C26 C25 C24 118.1(9) . . ?
C25 C26 C27 122.8(10) . . ?
C26 C27 C28 117.4(9) . . ?
C23 C28 C27 121.8(6) . . ?
C1 N1 C2 104.4(5) . . ?
C1 N1 Ni 125.4(4) . . ?
C2 N1 Ni 128.5(4) . . ?
C1 N2 C3 106.7(5) . . ?
N2 C1 N1 112.3(6) . . ?
C2 C3 N2 106.5(6) . . ?
C3 C2 N1 110.0(6) . . ?
C4 N3 C5 103.0(5) . . ?
C4 N3 Ni 126.0(5) . . ?
C5 N3 Ni 129.5(4) . . ?
C4 N4 C6 107.4(5) . . ?
N3 C4 N4 113.9(6) . . ?
N4 C6 C5 104.5(5) . . ?
N3 C5 C6 111.1(5) . . ?
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
Ni O21 2.027(4) . ?
Ni O11 2.029(3) . ?
Ni N3 2.031(4) . ?
Ni N1 2.034(4) . ?
Ni O23 2.109(4) . ?
Ni O13 2.122(4) . ?
O11 C11 1.249(5) . ?
O12 C11 1.245(6) . ?
O13 C12 1.404(6) . ?
C11 C12 1.557(6) . ?
C12 C13 1.511(6) . ?
C13 C14 1.351(7) . ?
C13 C18 1.381(7) . ?
C14 C15 1.395(8) . ?
C15 C16 1.339(9) . ?
C16 C17 1.348(8) . ?
C17 C18 1.381(8) . ?
O21 C21 1.247(5) . ?
O22 C21 1.265(6) . ?
O23 C22 1.415(5) . ?
C21 C22 1.531(6) . ?
C22 C23 1.502(6) . ?
C23 C28 1.361(7) . ?
C23 C24 1.377(7) . ?
C24 C25 1.398(9) . ?
C25 C26 1.339(10) . ?
C26 C27 1.369(10) . ?
C27 C28 1.416(8) . ?
N1 C1 1.324(6) . ?
N1 C2 1.357(6) . ?
N2 C1 1.315(6) . ?
N2 C3 1.359(7) . ?
C3 C2 1.340(7) . ?
N3 C4 1.300(6) . ?
N3 C5 1.367(6) . ?
N4 C4 1.324(6) . ?
N4 C6 1.347(6) . ?
C6 C5 1.368(6) . ?
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
C28 H28 O23 0.93 2.44 2.782(8) 101.8 .
O13 H13 O22 0.876(19) 1.77(2) 2.620(5) 162(5) 2_556
O23 H23 O12 0.906(19) 1.72(2) 2.621(5) 173(5) 2_566
N2 H20 O22 0.86 2.00 2.812(6) 158.2 2_656
N4 H40 O12 0.86 1.99 2.827(5) 163.3 2_666
