#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/78/2227803.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_2227803
loop_
_publ_author_name
'Jamshidvand, Arezoo'
'Kargar, Hadi'
'Kia, Reza'
'Tahir, Muhammad Nawaz'
_publ_section_title
;
 {6,6'-Diethoxy-2,2'-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenolato}copper(II)
;
_journal_coeditor_code           LH5150
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1473
_journal_paper_doi               10.1107/S1600536810042789
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Cu (C26 H26 N2 O4)]'
_chemical_formula_moiety         'C26 H26 Cu N2 O4'
_chemical_formula_sum            'C26 H26 Cu N2 O4'
_chemical_formula_weight         494.03
_chemical_name_systematic
{6,6'-Diethoxy-2,2'-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenolato}copper(II)
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 119.285(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.9755(7)
_cell_length_b                   15.8803(7)
_cell_length_c                   12.2264(6)
_cell_measurement_reflns_used    2273
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.54
_cell_volume                     2536.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_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  0.049
_diffrn_reflns_av_sigmaI/netI    0.0767
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3157
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.9815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0663
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0549P)²+4.1197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1468
_reflns_number_gt                1910
_reflns_number_total             3157
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5150.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2227803
_cod_database_fobs_code          2227803
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
Cu Cu1 0.0000 0.51186(3) 0.2500 0.0401(2) Uani d SP 1.00 . .
O O1 0.06365(19) 0.42620(14) 0.2039(2) 0.0464(6) Uani d . 1 . .
N N1 0.0519(2) 0.60241(16) 0.1905(3) 0.0401(7) Uani d . 1 . .
O O2 0.1286(2) 0.28916(14) 0.1524(3) 0.0591(8) Uani d . 1 . .
C C1 0.1134(3) 0.4353(2) 0.1421(3) 0.0395(8) Uani d . 1 . .
C C2 0.1501(3) 0.3619(2) 0.1111(3) 0.0444(9) Uani d . 1 . .
C C3 0.2022(3) 0.3667(3) 0.0445(4) 0.0548(10) Uani d . 1 . .
H H3A 0.2271 0.3177 0.0272 0.066 Uiso calc R 1 . .
C C4 0.2178(3) 0.4435(3) 0.0029(4) 0.0590(11) Uani d . 1 . .
H H4A 0.2514 0.4457 -0.0440 0.071 Uiso calc R 1 . .
C C5 0.1843(3) 0.5156(3) 0.0305(4) 0.0531(10) Uani d . 1 . .
H H5A 0.1958 0.5670 0.0028 0.064 Uiso calc R 1 . .
C C6 0.1315(3) 0.5138(2) 0.1013(3) 0.0411(8) Uani d . 1 . .
C C7 0.0998(3) 0.5921(2) 0.1269(3) 0.0449(9) Uani d . 1 . .
H H7A 0.1145 0.6403 0.0954 0.054 Uiso calc R 1 . .
C C8 0.0270(3) 0.6835(2) 0.2165(3) 0.0436(9) Uani d . 1 . .
C C9 0.0525(3) 0.7599(2) 0.1837(4) 0.0544(10) Uani d . 1 . .
H H9A 0.0881 0.7601 0.1392 0.065 Uiso calc R 1 . .
C C10 0.0264(3) 0.8356(2) 0.2158(4) 0.0621(13) Uani d . 1 . .
C C11 0.0545(4) 0.9164(3) 0.1760(5) 0.0899(18) Uani d . 1 . .
H H11A 0.0925 0.9516 0.2481 0.135 Uiso calc R 1 . .
H H11B -0.0067 0.9451 0.1169 0.135 Uiso calc R 1 . .
H H11C 0.0957 0.9041 0.1376 0.135 Uiso calc R 1 . .
C C12 0.1611(3) 0.2112(2) 0.1270(4) 0.0537(10) Uani d . 1 . .
H H12A 0.2352 0.2095 0.1671 0.064 Uiso calc R 1 . .
H H12B 0.1336 0.2044 0.0373 0.064 Uiso calc R 1 . .
C C13 0.1234(4) 0.1426(3) 0.1764(5) 0.0774(14) Uani d . 1 . .
H H13A 0.1490 0.0896 0.1659 0.116 Uiso calc R 1 . .
H H13B 0.0499 0.1419 0.1313 0.116 Uiso calc R 1 . .
H H13C 0.1469 0.1521 0.2638 0.116 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O1 2 . 88.42(14) ?
O1 Cu1 N1 2 2 93.93(11) ?
O1 Cu1 N1 . 2 174.47(11) ?
O1 Cu1 N1 2 . 174.47(11) ?
O1 Cu1 N1 . . 93.93(11) ?
N1 Cu1 N1 2 . 84.17(17) ?
C1 O1 Cu1 . . 127.2(2) ?
C7 N1 C8 . . 122.0(3) ?
C7 N1 Cu1 . . 124.8(2) ?
C8 N1 Cu1 . . 113.1(2) ?
C2 O2 C12 . . 119.4(3) ?
O1 C1 C2 . . 118.0(3) ?
O1 C1 C6 . . 124.3(3) ?
C2 C1 C6 . . 117.6(3) ?
O2 C2 C3 . . 124.8(3) ?
O2 C2 C1 . . 114.0(3) ?
C3 C2 C1 . . 121.2(3) ?
C2 C3 C4 . . 120.7(4) ?
C2 C3 H3A . . 119.6 ?
C4 C3 H3A . . 119.6 ?
C5 C4 C3 . . 120.2(4) ?
C5 C4 H4A . . 119.9 ?
C3 C4 H4A . . 119.9 ?
C4 C5 C6 . . 121.0(4) ?
C4 C5 H5A . . 119.5 ?
C6 C5 H5A . . 119.5 ?
C1 C6 C7 . . 123.4(3) ?
C1 C6 C5 . . 119.2(3) ?
C7 C6 C5 . . 117.3(3) ?
N1 C7 C6 . . 125.7(3) ?
N1 C7 H7A . . 117.2 ?
C6 C7 H7A . . 117.2 ?
C9 C8 C8 . 2 119.1(2) ?
C9 C8 N1 . . 126.1(4) ?
C8 C8 N1 2 . 114.82(19) ?
C10 C9 C8 . . 121.6(4) ?
C10 C9 H9A . . 119.2 ?
C8 C9 H9A . . 119.2 ?
C9 C10 C10 . 2 119.4(3) ?
C9 C10 C11 . . 119.2(4) ?
C10 C10 C11 2 . 121.4(3) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O2 C12 C13 . . 108.2(3) ?
O2 C12 H12A . . 110.1 ?
C13 C12 H12A . . 110.1 ?
O2 C12 H12B . . 110.1 ?
C13 C12 H12B . . 110.1 ?
H12A C12 H12B . . 108.4 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
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
Cu1 O1 2 1.898(2) ?
Cu1 O1 . 1.898(2) ?
Cu1 N1 2 1.938(3) ?
Cu1 N1 . 1.938(3) ?
O1 C1 . 1.303(4) ?
N1 C7 . 1.301(5) ?
N1 C8 . 1.419(4) ?
O2 C2 . 1.361(4) ?
O2 C12 . 1.419(4) ?
C1 C2 . 1.417(5) ?
C1 C6 . 1.417(5) ?
C2 C3 . 1.378(5) ?
C3 C4 . 1.385(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.358(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.430(5) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.419(5) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.389(5) ?
C8 C8 2 1.406(7) ?
C9 C10 . 1.379(5) ?
C9 H9A . 0.9300 ?
C10 C10 2 1.404(9) ?
C10 C11 . 1.504(5) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.484(6) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
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
O1 Cu1 O1 C1 2 . . . 169.0(3) ?
N1 Cu1 O1 C1 . . . . -6.0(3) ?
O1 Cu1 N1 C7 . . . . 8.1(3) ?
N1 Cu1 N1 C7 2 . . . -177.1(4) ?
O1 Cu1 N1 C8 . . . . -175.5(2) ?
N1 Cu1 N1 C8 2 . . . -0.69(17) ?
Cu1 O1 C1 C2 . . . . -176.4(2) ?
Cu1 O1 C1 C6 . . . . 2.2(5) ?
C12 O2 C2 C3 . . . . 0.1(6) ?
C12 O2 C2 C1 . . . . 179.8(3) ?
O1 C1 C2 O2 . . . . -0.6(5) ?
C6 C1 C2 O2 . . . . -179.3(3) ?
O1 C1 C2 C3 . . . . 179.1(3) ?
C6 C1 C2 C3 . . . . 0.5(5) ?
O2 C2 C3 C4 . . . . 178.0(4) ?
C1 C2 C3 C4 . . . . -1.7(6) ?
C2 C3 C4 C5 . . . . 1.8(7) ?
C3 C4 C5 C6 . . . . -0.6(6) ?
O1 C1 C6 C7 . . . . 2.0(6) ?
C2 C1 C6 C7 . . . . -179.4(3) ?
O1 C1 C6 C5 . . . . -177.9(3) ?
C2 C1 C6 C5 . . . . 0.7(5) ?
C4 C5 C6 C1 . . . . -0.6(6) ?
C4 C5 C6 C7 . . . . 179.5(3) ?
C8 N1 C7 C6 . . . . 177.1(3) ?
Cu1 N1 C7 C6 . . . . -6.9(5) ?
C1 C6 C7 N1 . . . . 0.7(6) ?
C5 C6 C7 N1 . . . . -179.4(3) ?
C7 N1 C8 C9 . . . . -2.6(6) ?
Cu1 N1 C8 C9 . . . . -179.1(3) ?
C7 N1 C8 C8 . . . 2 178.5(4) ?
Cu1 N1 C8 C8 . . . 2 2.0(5) ?
C8 C8 C9 C10 2 . . . 0.2(6) ?
N1 C8 C9 C10 . . . . -178.7(3) ?
C8 C9 C10 C10 . . . 2 0.7(7) ?
C8 C9 C10 C11 . . . . -179.0(4) ?
C2 O2 C12 C13 . . . . -177.2(4) ?
