#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/31/2223190.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_2223190
loop_
_publ_author_name
'Wang, Yun'
'Zhu, Li-Li'
'Sun, Bai-Wang'
_publ_section_title
;
 Bis{2-methoxy-6-[(3-pyridyl)methyliminomethyl]phenolato}copper(II)
;
_journal_coeditor_code           RZ2354
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1058
_journal_paper_doi               10.1107/S1600536809029523
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (C14 H13 N2 O2)2]'
_chemical_formula_moiety         'C28 H26 Cu N4 O4'
_chemical_formula_sum            'C28 H26 Cu N4 O4'
_chemical_formula_weight         546.07
_chemical_name_systematic
;
Bis{2-methoxy-6-[(3-pyridyl)methyliminomethyl]phenolato}copper(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                 102.55(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.455(2)
_cell_length_b                   14.414(3)
_cell_length_c                   7.5491(15)
_cell_measurement_reflns_used    10382
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.480
_cell_measurement_theta_min      3.19
_cell_volume                     1216.7(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.96
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11771
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_T_max  0.828
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             566
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.616
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.409
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.409
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0346
_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)+(0.0515P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                2430
_reflns_number_total             2667
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2354.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223190
_cod_database_fobs_code          2223190
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_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 1.0000 1.0000 0.0000 0.03101(13) Uani d S 1 . .
N N1 0.94828(11) 1.08186(9) -0.22373(17) 0.0269(3) Uani d . 1 . .
C C14 1.04327(16) 1.27619(11) -0.3538(2) 0.0346(4) Uani d . 1 . .
H H14A 0.9670 1.2747 -0.4280 0.041 Uiso calc R 1 . .
C C9 1.02998(15) 1.10214(10) -0.3470(2) 0.0307(4) Uani d . 1 . .
H H9A 0.9841 1.1069 -0.4708 0.037 Uiso calc R 1 . .
H H9B 1.0867 1.0517 -0.3417 0.037 Uiso calc R 1 . .
C C11 1.20928(16) 1.19482(12) -0.1813(2) 0.0359(4) Uani d . 1 . .
H H11A 1.2487 1.1403 -0.1375 0.043 Uiso calc R 1 . .
C C7 0.74950(13) 1.11896(10) -0.1721(2) 0.0294(4) Uani d . 1 . .
O O1 0.67391(12) 1.03058(10) 0.23920(19) 0.0457(3) Uani d . 1 . .
C C8 0.84437(15) 1.11952(11) -0.2697(2) 0.0308(4) Uani d . 1 . .
H H8A 0.8285 1.1511 -0.3798 0.037 Uiso calc R 1 . .
C C10 1.09654(14) 1.19174(11) -0.2930(2) 0.0284(3) Uani d . 1 . .
N N2 1.09381(14) 1.35872(10) -0.3131(2) 0.0413(4) Uani d . 1 . .
C C3 0.65892(13) 1.07713(11) 0.0778(2) 0.0315(4) Uani d . 1 . .
C C6 0.64554(16) 1.17021(12) -0.2470(3) 0.0380(4) Uani d . 1 . .
H H6A 0.6412 1.2022 -0.3552 0.046 Uiso calc R 1 . .
C C4 0.55774(15) 1.12611(12) 0.0004(3) 0.0379(4) Uani d . 1 . .
H H4A 0.4931 1.1278 0.0566 0.045 Uiso calc R 1 . .
C C13 1.20181(17) 1.35935(13) -0.2044(3) 0.0416(4) Uani d . 1 . .
H H13A 1.2384 1.4164 -0.1730 0.050 Uiso calc R 1 . .
C C5 0.55195(16) 1.17370(13) -0.1642(3) 0.0424(5) Uani d . 1 . .
H H5A 0.4839 1.2075 -0.2160 0.051 Uiso calc R 1 . .
C C1 0.58255(19) 1.03860(17) 0.3375(3) 0.0501(5) Uani d . 1 . .
H H1A 0.6037 1.0030 0.4473 0.075 Uiso calc R 1 . .
H H1B 0.5088 1.0157 0.2651 0.075 Uiso calc R 1 . .
H H1C 0.5731 1.1026 0.3670 0.075 Uiso calc R 1 . .
C C12 1.26288(17) 1.28035(13) -0.1354(3) 0.0426(4) Uani d . 1 . .
H H12A 1.3385 1.2843 -0.0595 0.051 Uiso calc R 1 . .
O O2 0.85152(11) 1.02297(9) 0.07153(19) 0.0383(3) Uani d . 1 . .
C C2 0.75880(13) 1.07128(10) -0.0065(2) 0.0287(3) Uani d . 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
O2 Cu1 O2 3_775 . 180.0 ?
O2 Cu1 N1 3_775 . 89.00(6) ?
O2 Cu1 N1 . . 91.00(6) ?
O2 Cu1 N1 3_775 3_775 91.00(6) ?
O2 Cu1 N1 . 3_775 89.00(6) ?
N1 Cu1 N1 . 3_775 180.00(6) ?
C8 N1 C9 . . 114.85(13) ?
C8 N1 Cu1 . . 123.58(12) ?
C9 N1 Cu1 . . 121.57(10) ?
N2 C14 C10 . . 124.60(17) ?
N2 C14 H14A . . 117.7 ?
C10 C14 H14A . . 117.7 ?
N1 C9 C10 . . 110.44(12) ?
N1 C9 H9A . . 109.6 ?
C10 C9 H9A . . 109.6 ?
N1 C9 H9B . . 109.6 ?
C10 C9 H9B . . 109.6 ?
H9A C9 H9B . . 108.1 ?
C10 C11 C12 . . 119.04(16) ?
C10 C11 H11A . . 120.5 ?
C12 C11 H11A . . 120.5 ?
C6 C7 C2 . . 120.31(16) ?
C6 C7 C8 . . 117.23(15) ?
C2 C7 C8 . . 122.44(14) ?
C3 O1 C1 . . 117.61(15) ?
N1 C8 C7 . . 128.12(15) ?
N1 C8 H8A . . 115.9 ?
C7 C8 H8A . . 115.9 ?
C11 C10 C14 . . 117.21(15) ?
C11 C10 C9 . . 122.86(14) ?
C14 C10 C9 . . 119.92(15) ?
C13 N2 C14 . . 116.70(16) ?
O1 C3 C4 . . 124.16(16) ?
O1 C3 C2 . . 114.21(14) ?
C4 C3 C2 . . 121.63(16) ?
C5 C6 C7 . . 121.24(17) ?
C5 C6 H6A . . 119.4 ?
C7 C6 H6A . . 119.4 ?
C3 C4 C5 . . 119.95(17) ?
C3 C4 H4A . . 120.0 ?
C5 C4 H4A . . 120.0 ?
N2 C13 C12 . . 123.81(17) ?
N2 C13 H13A . . 118.1 ?
C12 C13 H13A . . 118.1 ?
C6 C5 C4 . . 119.92(16) ?
C6 C5 H5A . . 120.0 ?
C4 C5 H5A . . 120.0 ?
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C13 C12 C11 . . 118.62(17) ?
C13 C12 H12A . . 120.7 ?
C11 C12 H12A . . 120.7 ?
C2 O2 Cu1 . . 130.63(12) ?
O2 C2 C7 . . 124.05(15) ?
O2 C2 C3 . . 119.02(15) ?
C7 C2 C3 . . 116.93(14) ?
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 O2 3_775 1.9218(13) ?
Cu1 O2 . 1.9218(13) ?
Cu1 N1 . 2.0399(13) ?
Cu1 N1 3_775 2.0399(13) ?
N1 C8 . 1.285(2) ?
N1 C9 . 1.485(2) ?
C14 N2 . 1.329(2) ?
C14 C10 . 1.394(2) ?
C14 H14A . 0.9300 ?
C9 C10 . 1.510(2) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C11 C10 . 1.381(2) ?
C11 C12 . 1.387(2) ?
C11 H11A . 0.9300 ?
C7 C6 . 1.411(2) ?
C7 C2 . 1.411(2) ?
C7 C8 . 1.439(2) ?
O1 C3 . 1.369(2) ?
O1 C1 . 1.413(2) ?
C8 H8A . 0.9300 ?
N2 C13 . 1.328(2) ?
C3 C4 . 1.374(2) ?
C3 C2 . 1.427(2) ?
C6 C5 . 1.354(3) ?
C6 H6A . 0.9300 ?
C4 C5 . 1.408(3) ?
C4 H4A . 0.9300 ?
C13 C12 . 1.378(3) ?
C13 H13A . 0.9300 ?
C5 H5A . 0.9300 ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C12 H12A . 0.9300 ?
O2 C2 . 1.2993(18) ?
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
C9 H9B O2 3_775 0.97 2.28 2.862(2) 118
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
O2 Cu1 N1 C8 3_775 . . . 175.74(14) ?
O2 Cu1 N1 C8 . . . . -4.26(14) ?
O2 Cu1 N1 C9 3_775 . . . -4.15(11) ?
O2 Cu1 N1 C9 . . . . 175.85(11) ?
C8 N1 C9 C10 . . . . 86.53(17) ?
Cu1 N1 C9 C10 . . . . -93.57(13) ?
C9 N1 C8 C7 . . . . -174.86(15) ?
Cu1 N1 C8 C7 . . . . 5.3(2) ?
C6 C7 C8 N1 . . . . 176.48(16) ?
C2 C7 C8 N1 . . . . -2.3(3) ?
C12 C11 C10 C14 . . . . 0.2(3) ?
C12 C11 C10 C9 . . . . -178.60(16) ?
N2 C14 C10 C11 . . . . 0.7(3) ?
N2 C14 C10 C9 . . . . 179.51(16) ?
N1 C9 C10 C11 . . . . 94.88(18) ?
N1 C9 C10 C14 . . . . -83.88(18) ?
C10 C14 N2 C13 . . . . -1.1(3) ?
C1 O1 C3 C4 . . . . -4.3(3) ?
C1 O1 C3 C2 . . . . 175.52(16) ?
C2 C7 C6 C5 . . . . -1.1(3) ?
C8 C7 C6 C5 . . . . -179.88(16) ?
O1 C3 C4 C5 . . . . 178.43(17) ?
C2 C3 C4 C5 . . . . -1.4(3) ?
C14 N2 C13 C12 . . . . 0.8(3) ?
C7 C6 C5 C4 . . . . 0.4(3) ?
C3 C4 C5 C6 . . . . 0.8(3) ?
N2 C13 C12 C11 . . . . 0.0(3) ?
C10 C11 C12 C13 . . . . -0.5(3) ?
N1 Cu1 O2 C2 . . . . 1.65(16) ?
N1 Cu1 O2 C2 3_775 . . . -178.35(16) ?
Cu1 O2 C2 C7 . . . . 0.5(3) ?
Cu1 O2 C2 C3 . . . . -179.78(12) ?
C6 C7 C2 O2 . . . . -179.72(16) ?
C8 C7 C2 O2 . . . . -1.0(3) ?
C6 C7 C2 C3 . . . . 0.5(2) ?
C8 C7 C2 C3 . . . . 179.25(14) ?
O1 C3 C2 O2 . . . . 1.1(2) ?
C4 C3 C2 O2 . . . . -179.07(16) ?
O1 C3 C2 C7 . . . . -179.13(14) ?
C4 C3 C2 C7 . . . . 0.7(2) ?
