#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/66/2006690.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_2006690
loop_
_publ_author_name
'Warda, Salam A.'
_publ_section_title
;(Imidazole-N³)(N-salicylidene-α-aminoisobutyrato-O,N,O')copper(II)
 Dimer
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1588
_journal_page_last               1590
_journal_paper_doi               10.1107/S0108270197008275
_journal_volume                  53
_journal_year                    1997
_chemical_formula_iupac          '[Cu (C11 H11 N O3) (C3 H4 N2)]'
_chemical_formula_sum            'C14 H15 Cu N3 O3'
_chemical_formula_weight         336.83
_chemical_name_systematic
;
 (Imidazole) (N-Salicylidene-α-aminoisobutyrato)-Copper(II) Dimer
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 94.489(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1844(4)
_cell_length_b                   16.9279(7)
_cell_length_c                   9.3097(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.617
_cell_measurement_theta_min      40.475
_cell_volume                     1442.96(11)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD-4 (Harms, 1997)'
_computing_molecular_graphics    'XP (Siemens, 1996b)'
_computing_publication_material  SHELXL96
_computing_structure_refinement  'SHELXL96 (Sheldrick, 1996b)'
_computing_structure_solution    'SHELXS96 (Sheldrick, 1996a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf Nonius CAD4'
_diffrn_measurement_method       'ω--2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0108
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2286
_diffrn_reflns_theta_max         59.95
_diffrn_reflns_theta_min         4.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.265
_exptl_absorpt_correction_T_max  0.8459
_exptl_absorpt_correction_T_min  0.4759
_exptl_absorpt_correction_type
'empirical, psi-scans (XPREP; Siemens, 1996a)'
_exptl_crystal_colour            Violet
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.359
_refine_ls_extinction_coef       0.0025(3)
_refine_ls_extinction_method     'SHELXL96 (Sheldrick, 1996b)'
_refine_ls_goodness_of_fit_all   1.087
_refine_ls_goodness_of_fit_obs   1.098
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_restrained_S_obs      1.098
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_obs          .0338
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0507P)²+1.3387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0932
_refine_ls_wR_factor_obs         .0924
_reflns_number_observed          2064
_reflns_number_total             2140
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jz1216.cif
_cod_data_source_block           sabim
_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:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0507P)^2^+1.3387P] 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^)+(0.0507P)^2^+1.3387P] 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 21/c'
_cod_database_code               2006690
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
Cu .88079(4) .42577(2) -.00863(4) .03248(19) Uani d . 1 . Cu
O1 1.0478(2) .43942(11) -.1167(2) .0383(4) Uani d . 1 . O
N1 .9781(2) .35135(12) .1239(2) .0328(5) Uani d . 1 . N
C1 1.1630(3) .39304(15) -.1122(3) .0338(6) Uani d . 1 . C
O2 .7209(2) .41458(11) .1148(2) .0399(5) Uani d . 1 . O
N2 .7548(2) .47596(13) -.1623(2) .0343(5) Uani d . 1 . N
C2 1.2649(3) .40325(18) -.2169(3) .0422(7) Uani d . 1 . C
H2 1.2464 .4409 -.2887 .051 Uiso calc R 1 . H
O3 .6669(2) .36980(15) .3283(2) .0620(7) Uani d . 1 . O
N3 .5791(2) .54319(15) -.2774(2) .0409(5) Uani d . 1 . N
H31 .5023 .5719 -.2932 .049 Uiso calc R 1 . H
C3 1.3900(3) .35913(18) -.2154(3) .0490(7) Uani d . 1 . C
H3 1.4553 .3680 -.2851 .059 Uiso calc R 1 . H
C4 1.4208(3) .3015(2) -.1119(4) .0566(9) Uani d . 1 . C
H4 1.5054 .2713 -.1121 .068 Uiso calc R 1 . H
C5 1.3243(3) .28984(18) -.0093(4) .0491(7) Uani d . 1 . C
H5 1.3447 .2513 .0607 .059 Uiso calc R 1 . H
C6 1.1943(3) .33448(16) -.0062(3) .0366(6) Uani d . 1 . C
C7 1.1033(3) .31932(16) .1087(3) .0376(6) Uani d . 1 . C
H7 1.1375 .2832 .1787 .045 Uiso calc R 1 . H
C8 .8960(3) .33083(16) .2494(3) .0367(6) Uani d . 1 . C
C9 .7499(3) .37526(16) .2302(3) .0391(6) Uani d . 1 . C
C10 .9795(4) .3579(2) .3885(3) .0541(8) Uani d . 1 . C
H10A .9985 .4135 .3833 .081 Uiso calc R 1 . H
H10B 1.0704 .3298 .4015 .081 Uiso calc R 1 . H
H10C .9223 .3474 .4684 .081 Uiso calc R 1 . H
C11 .8606(3) .24262(17) .2520(4) .0517(8) Uani d . 1 . C
H11A .8065 .2281 .1635 .078 Uiso calc R 1 . H
H11B .8032 .2315 .3315 .078 Uiso calc R 1 . H
H11C .9498 .2129 .2626 .078 Uiso calc R 1 . H
C12 .6347(3) .51737(16) -.1503(3) .0361(6) Uani d . 1 . C
H12 .5941 .5272 -.0636 .043 Uiso calc R 1 . H
C13 .6662(3) .5158(2) -.3779(3) .0556(8) Uani d . 1 . C
H13 .6533 .5238 -.4770 .067 Uiso calc R 1 . H
C14 .7746(3) .4750(2) -.3067(3) .0484(7) Uani d . 1 . C
H14 .8509 .4500 -.3486 .058 Uiso calc R 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu N1 . 93.69(8) y
O1 Cu O2 . 175.40(8) y
N1 Cu O2 . 83.83(8) y
O1 Cu N2 . 90.90(8) y
N1 Cu N2 . 164.74(9) y
O2 Cu N2 . 92.48(8) y
O1 Cu O1 3_765 86.89(7) y
N1 Cu O1 3_765 101.31(8) y
O2 Cu O1 3_765 89.78(7) y
N2 Cu O1 3_765 93.46(8) y
C1 O1 Cu . 125.97(16) ?
C7 N1 C8 . 120.1(2) ?
C7 N1 Cu . 125.22(18) ?
C8 N1 Cu . 114.68(16) ?
O1 C1 C6 . 124.1(2) ?
O1 C1 C2 . 118.7(2) ?
C6 C1 C2 . 117.3(2) ?
C9 O2 Cu . 115.56(16) ?
C12 N2 C14 . 105.4(2) ?
C12 N2 Cu . 128.14(18) ?
C14 N2 Cu . 126.45(18) ?
C3 C2 C1 . 121.8(3) ?
C3 C2 H2 . 119.11(18) ?
C1 C2 H2 . 119.11(17) ?
C12 N3 C13 . 107.2(2) ?
C12 N3 H31 . 126.38(15) ?
C13 N3 H31 . 126.38(16) ?
C2 C3 C4 . 121.1(3) ?
C2 C3 H3 . 119.45(18) ?
C4 C3 H3 . 119.45(16) ?
C5 C4 C3 . 118.6(3) ?
C5 C4 H4 . 120.68(19) ?
C3 C4 H4 . 120.68(16) ?
C4 C5 C6 . 122.1(3) ?
C4 C5 H5 . 118.94(19) ?
C6 C5 H5 . 118.94(17) ?
C1 C6 C5 . 119.1(2) ?
C1 C6 C7 . 123.3(2) ?
C5 C6 C7 . 117.5(3) ?
N1 C7 C6 . 125.7(2) ?
N1 C7 H7 . 117.13(15) ?
C6 C7 H7 . 117.13(15) ?
N1 C8 C10 . 110.3(2) ?
N1 C8 C11 . 111.3(2) ?
C10 C8 C11 . 111.9(3) ?
N1 C8 C9 . 106.7(2) ?
C10 C8 C9 . 109.2(2) ?
C11 C8 C9 . 107.2(2) ?
O3 C9 O2 . 124.1(2) ?
O3 C9 C8 . 117.4(2) ?
O2 C9 C8 . 118.5(2) ?
C8 C10 H10A . 109.47(17) ?
C8 C10 H10B . 109.47(16) ?
H10A C10 H10B . 109.5 ?
C8 C10 H10C . 109.47(15) ?
H10A C10 H10C . 109.5 ?
H10B C10 H10C . 109.5 ?
C8 C11 H11A . 109.47(17) ?
C8 C11 H11B . 109.47(15) ?
H11A C11 H11B . 109.5 ?
C8 C11 H11C . 109.47(15) ?
H11A C11 H11C . 109.5 ?
H11B C11 H11C . 109.5 ?
N2 C12 N3 . 111.4(2) ?
N2 C12 H12 . 124.29(15) ?
N3 C12 H12 . 124.29(15) ?
C14 C13 N3 . 106.7(3) ?
C14 C13 H13 . 126.63(17) ?
N3 C13 H13 . 126.63(16) ?
C13 C14 N2 . 109.2(2) ?
C13 C14 H14 . 125.42(17) ?
N2 C14 H14 . 125.42(15) ?
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
Cu O1 . 1.9127(18) y
Cu N1 . 1.933(2) y
Cu O2 . 1.9434(18) y
Cu N2 . 1.962(2) y
Cu O1 3_765 2.623(2) y
O1 C1 . 1.316(3) ?
N1 C7 . 1.289(3) ?
N1 C8 . 1.481(3) ?
C1 C6 . 1.413(4) ?
C1 C2 . 1.413(4) ?
O2 C9 . 1.275(3) ?
N2 C12 . 1.319(3) ?
N2 C14 . 1.370(3) ?
C2 C3 . 1.370(4) ?
C2 H2 . .9300 ?
O3 C9 . 1.238(3) ?
N3 C12 . 1.325(3) ?
N3 C13 . 1.360(4) ?
N3 H31 . .8600 ?
C3 C4 . 1.386(5) ?
C3 H3 . .9300 ?
C4 C5 . 1.367(4) ?
C4 H4 . .9300 ?
C5 C6 . 1.415(4) ?
C5 H5 . .9300 ?
C6 C7 . 1.432(4) ?
C7 H7 . .9300 ?
C8 C10 . 1.523(4) ?
C8 C11 . 1.529(4) ?
C8 C9 . 1.536(4) ?
C10 H10A . .9600 ?
C10 H10B . .9600 ?
C10 H10C . .9600 ?
C11 H11A . .9600 ?
C11 H11B . .9600 ?
C11 H11C . .9600 ?
C12 H12 . .9300 ?
C13 C14 . 1.344(4) ?
C13 H13 . .9300 ?
C14 H14 . .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
N3 H31 O3 1_665 0.86 1.85 2.707(3) 178 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
N1 Cu O1 C1 . 15.7(2)
O2 Cu O1 C1 . 73.0(10)
N2 Cu O1 C1 . -149.8(2)
O1 Cu O1 C1 3_765 116.8(2)
O1 Cu N1 C7 . -10.1(2)
O2 Cu N1 C7 . 173.8(2)
N2 Cu N1 C7 . 97.1(4)
O1 Cu N1 C7 3_765 -97.7(2)
O1 Cu N1 C8 . 170.89(18)
O2 Cu N1 C8 . -5.21(18)
N2 Cu N1 C8 . -81.9(4)
O1 Cu N1 C8 3_765 83.33(18)
Cu O1 C1 C6 . -12.9(4)
Cu O1 C1 C2 . 168.91(19)
O1 Cu O2 C9 . -49.6(10)
N1 Cu O2 C9 . 8.1(2)
N2 Cu O2 C9 . 173.2(2)
O1 Cu O2 C9 3_765 -93.3(2)
O1 Cu N2 C12 . -150.0(2)
N1 Cu N2 C12 . 102.4(4)
O2 Cu N2 C12 . 26.9(2)
O1 Cu N2 C12 3_765 -63.1(2)
O1 Cu N2 C14 . 29.9(2)
N1 Cu N2 C14 . -77.6(4)
O2 Cu N2 C14 . -153.2(2)
O1 Cu N2 C14 3_765 116.9(2)
O1 C1 C2 C3 . 177.5(3)
C6 C1 C2 C3 . -0.8(4)
C1 C2 C3 C4 . 1.0(5)
C2 C3 C4 C5 . -0.7(5)
C3 C4 C5 C6 . 0.3(5)
O1 C1 C6 C5 . -177.9(3)
C2 C1 C6 C5 . 0.3(4)
O1 C1 C6 C7 . -0.1(4)
C2 C1 C6 C7 . 178.1(3)
C4 C5 C6 C1 . -0.1(5)
C4 C5 C6 C7 . -178.0(3)
C8 N1 C7 C6 . -179.3(2)
Cu N1 C7 C6 . 1.8(4)
C1 C6 C7 N1 . 6.0(4)
C5 C6 C7 N1 . -176.1(3)
C7 N1 C8 C10 . 64.6(3)
Cu N1 C8 C10 . -116.4(2)
C7 N1 C8 C11 . -60.3(3)
Cu N1 C8 C11 . 118.7(2)
C7 N1 C8 C9 . -177.0(2)
Cu N1 C8 C9 . 2.1(3)
Cu O2 C9 O3 . 171.6(2)
Cu O2 C9 C8 . -9.2(3)
N1 C8 C9 O3 . -176.1(3)
C10 C8 C9 O3 . -56.9(3)
C11 C8 C9 O3 . 64.5(3)
N1 C8 C9 O2 . 4.6(3)
C10 C8 C9 O2 . 123.8(3)
C11 C8 C9 O2 . -114.8(3)
C14 N2 C12 N3 . -0.8(3)
Cu N2 C12 N3 . 179.15(18)
C13 N3 C12 N2 . 1.2(3)
C12 N3 C13 C14 . -1.1(4)
N3 C13 C14 N2 . 0.7(4)
C12 N2 C14 C13 . 0.1(4)
Cu N2 C14 C13 . -179.9(2)
