#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/47/2224722.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_2224722
loop_
_publ_author_name
'Chen, Xiaodan'
'Sun, Yu'
'Yao, Qingzhao'
'Zhang, Huaihong'
'Liang, Qing'
_publ_section_title
Bis[2-methoxy-6-(3-pyridylmethyliminomethyl)phenolato-κ²N,O]copper(II)
_journal_coeditor_code           NK2015
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m39
_journal_paper_doi               10.1107/S1600536809052349
_journal_volume                  66
_journal_year                    2010
_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-pyridylmethyliminomethyl)phenolato-
κ²N,O]copper(II)
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.6890(10)
_cell_angle_beta                 91.3610(10)
_cell_angle_gamma                103.241(2)
_cell_formula_units_Z            1
_cell_length_a                   5.1750(10)
_cell_length_b                   10.7291(14)
_cell_length_c                   11.4369(15)
_cell_measurement_reflns_used    13380
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.020
_cell_measurement_theta_min      3.01
_cell_volume                     608.03(16)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'Thin-slice ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3054
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.942
_exptl_absorpt_correction_T_max  0.7718
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             283
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.399
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0374P)²+0.3354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                1908
_reflns_number_total             2101
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            nk2015.cif
_cod_data_source_block           I
_cod_database_code               2224722
_cod_database_fobs_code          2224722
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.5000 0.5000 0.5000 0.03467(17) Uani d S 1 . .
N N1 0.5603(4) 0.3229(2) 0.44427(19) 0.0374(5) Uani d . 1 . .
C C1 0.4647(5) 0.2520(3) 0.3428(2) 0.0396(6) Uani d . 1 . .
H H1 0.5277 0.1775 0.3201 0.048 Uiso calc R 1 . .
C C2 0.2735(5) 0.2746(3) 0.2613(2) 0.0386(6) Uani d . 1 . .
C C3 0.1569(5) 0.3815(3) 0.2862(2) 0.0352(6) Uani d . 1 . .
C C4 -0.0381(5) 0.3930(3) 0.2004(2) 0.0405(6) Uani d . 1 . .
C C5 -0.0989(6) 0.3047(3) 0.0952(3) 0.0501(8) Uani d . 1 . .
H H5 -0.2233 0.3144 0.0395 0.060 Uiso calc R 1 . .
C C6 0.0245(6) 0.2009(3) 0.0715(3) 0.0549(8) Uani d . 1 . .
H H6 -0.0175 0.1423 0.0002 0.066 Uiso calc R 1 . .
C C7 0.2054(6) 0.1856(3) 0.1523(3) 0.0503(7) Uani d . 1 . .
H H7 0.2857 0.1160 0.1362 0.060 Uiso calc R 1 . .
C C8 -0.3148(6) 0.5261(4) 0.1431(3) 0.0615(9) Uani d . 1 . .
H H8A -0.2139 0.5422 0.0755 0.092 Uiso calc R 1 . .
H H8B -0.3757 0.6021 0.1751 0.092 Uiso calc R 1 . .
H H8C -0.4650 0.4540 0.1191 0.092 Uiso calc R 1 . .
C C9 0.7366(6) 0.2684(3) 0.5141(2) 0.0413(6) Uani d . 1 . .
H H9A 0.8854 0.3376 0.5512 0.050 Uiso calc R 1 . .
H H9B 0.8068 0.2052 0.4614 0.050 Uiso calc R 1 . .
C C10 0.7083(8) 0.2181(3) 0.7196(3) 0.0675(10) Uani d . 1 . .
H H10 0.8760 0.2743 0.7354 0.081 Uiso d R 1 A .
C C11 0.5900(5) 0.2036(2) 0.6089(2) 0.0386(6) Uani d . 1 A .
C C12 0.3393(7) 0.1225(4) 0.5890(3) 0.0689(10) Uani d . 1 . .
H H12 0.2480 0.1087 0.5151 0.083 Uiso d R 1 A .
N N2 0.6057(10) 0.1590(4) 0.8074(3) 0.0946(16) Uani d P 0.70(4) A 1
C C13 0.2220(8) 0.0611(4) 0.6786(5) 0.0910(17) Uani d P 0.70(4) A 1
H H13A 0.0530 0.0057 0.6658 0.109 Uiso d PR 0.70(4) A 1
N N2' 0.2220(8) 0.0611(4) 0.6786(5) 0.0910(17) Uani d P 0.30(4) A 2
C C13' 0.6057(10) 0.1590(4) 0.8074(3) 0.0946(16) Uani d P 0.30(4) A 2
H H13B 0.6924 0.1680 0.8736 0.113 Uiso d PR 0.30(4) A 2
C C14 0.3650(12) 0.0834(5) 0.7849(4) 0.0863(14) Uani d . 1 . .
H H14 0.2856 0.0419 0.8446 0.104 Uiso d R 1 A .
O O1 0.2170(4) 0.47043(18) 0.38216(16) 0.0423(5) Uani d . 1 . .
O O2 -0.1501(4) 0.4964(2) 0.23188(18) 0.0514(5) 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'
O O 0.0106 0.0060 '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'
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_666 180.0000(10) ?
O1 Cu1 N1 . 2_666 88.69(8) y
O1 Cu1 N1 2_666 2_666 91.31(8) y
O1 Cu1 N1 . . 91.31(8) y
O1 Cu1 N1 2_666 . 88.69(8) y
N1 Cu1 N1 2_666 . 180.0000(10) ?
C1 N1 C9 . . 115.3(2) ?
C1 N1 Cu1 . . 123.32(19) ?
C9 N1 Cu1 . . 121.18(18) ?
N1 C1 C2 . . 127.6(3) ?
N1 C1 H1 . . 116.2 ?
C2 C1 H1 . . 116.2 ?
C3 C2 C7 . . 120.3(3) ?
C3 C2 C1 . . 121.9(2) ?
C7 C2 C1 . . 117.8(3) ?
O1 C3 C2 . . 124.0(2) ?
O1 C3 C4 . . 118.5(2) ?
C2 C3 C4 . . 117.5(2) ?
O2 C4 C5 . . 124.9(3) ?
O2 C4 C3 . . 114.6(2) ?
C5 C4 C3 . . 120.5(3) ?
C4 C5 C6 . . 120.7(3) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C7 C6 C5 . . 120.1(3) ?
C7 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
C6 C7 C2 . . 120.8(3) ?
C6 C7 H7 . . 119.6 ?
C2 C7 H7 . . 119.6 ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 C11 . . 111.4(2) ?
N1 C9 H9A . . 109.3 ?
C11 C9 H9A . . 109.3 ?
N1 C9 H9B . . 109.3 ?
C11 C9 H9B . . 109.3 ?
H9A C9 H9B . . 108.0 ?
N2 C10 C11 . . 125.9(4) ?
N2 C10 H10 . . 117.1 ?
C11 C10 H10 . . 117.0 ?
C10 C11 C12 . . 115.8(3) ?
C10 C11 C9 . . 120.7(3) ?
C12 C11 C9 . . 123.4(3) ?
C11 C12 C13 . . 120.2(4) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.8 ?
C14 N2 C10 . . 116.2(4) ?
C14 N2 H13B . . 121.7 ?
C10 N2 H13B . . 122.0 ?
C14 C13 C12 . . 117.6(4) ?
C14 C13 H13A . . 121.5 ?
C12 C13 H13A . . 120.9 ?
N2 C14 C13 . . 124.1(4) ?
N2 C14 H14 . . 118.6 ?
C13 C14 H14 . . 117.3 ?
C3 O1 Cu1 . . 129.26(17) ?
C4 O2 C8 . . 117.5(2) ?
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 . 1.9005(18) y
Cu1 O1 2_666 1.9005(18) y
Cu1 N1 2_666 1.997(2) y
Cu1 N1 . 1.997(2) y
N1 C1 . 1.294(3) ?
N1 C9 . 1.476(3) ?
C1 C2 . 1.432(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.406(4) ?
C2 C7 . 1.418(4) ?
C3 O1 . 1.306(3) ?
C3 C4 . 1.431(4) ?
C4 O2 . 1.366(3) ?
C4 C5 . 1.381(4) ?
C5 C6 . 1.397(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.356(4) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 O2 . 1.432(3) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C11 . 1.512(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 N2 . 1.333(5) ?
C10 C11 . 1.362(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.377(4) ?
C12 C13 . 1.389(5) ?
C12 H12 . 0.9301 ?
N2 C14 . 1.314(7) ?
N2 H13B . 0.8506 ?
C13 C14 . 1.364(7) ?
C13 H13A . 0.9305 ?
C14 H14 . 0.9300 ?
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 N1 C1 . . . . 15.6(2) ?
O1 Cu1 N1 C1 2_666 . . . -164.4(2) ?
N1 Cu1 N1 C1 2_666 . . . -14E1(10) ?
O1 Cu1 N1 C9 . . . . -169.17(19) ?
O1 Cu1 N1 C9 2_666 . . . 10.83(19) ?
N1 Cu1 N1 C9 2_666 . . . 3E1(10) ?
C9 N1 C1 C2 . . . . 174.5(2) ?
Cu1 N1 C1 C2 . . . . -9.9(4) ?
N1 C1 C2 C3 . . . . -1.8(4) ?
N1 C1 C2 C7 . . . . 177.6(3) ?
C7 C2 C3 O1 . . . . -177.1(2) ?
C1 C2 C3 O1 . . . . 2.2(4) ?
C7 C2 C3 C4 . . . . 2.5(4) ?
C1 C2 C3 C4 . . . . -178.1(2) ?
O1 C3 C4 O2 . . . . -2.5(3) ?
C2 C3 C4 O2 . . . . 177.9(2) ?
O1 C3 C4 C5 . . . . 177.0(2) ?
C2 C3 C4 C5 . . . . -2.7(4) ?
O2 C4 C5 C6 . . . . -179.3(3) ?
C3 C4 C5 C6 . . . . 1.3(4) ?
C4 C5 C6 C7 . . . . 0.3(4) ?
C5 C6 C7 C2 . . . . -0.5(5) ?
C3 C2 C7 C6 . . . . -1.0(4) ?
C1 C2 C7 C6 . . . . 179.6(3) ?
C1 N1 C9 C11 . . . . -99.3(3) ?
Cu1 N1 C9 C11 . . . . 85.1(2) ?
N2 C10 C11 C12 . . . . 1.6(6) ?
N2 C10 C11 C9 . . . . -175.3(4) ?
N1 C9 C11 C10 . . . . -139.2(3) ?
N1 C9 C11 C12 . . . . 44.1(4) ?
C10 C11 C12 C13 . . . . -0.1(5) ?
C9 C11 C12 C13 . . . . 176.7(3) ?
C11 C10 N2 C14 . . . . -2.3(7) ?
C11 C12 C13 C14 . . . . -0.7(6) ?
C10 N2 C14 C13 . . . . 1.4(7) ?
C12 C13 C14 N2 . . . . 0.0(7) ?
C2 C3 O1 Cu1 . . . . 10.5(4) ?
C4 C3 O1 Cu1 . . . . -169.14(17) ?
O1 Cu1 O1 C3 2_666 . . . -1E1(10) ?
N1 Cu1 O1 C3 2_666 . . . 163.5(2) ?
N1 Cu1 O1 C3 . . . . -16.5(2) ?
C5 C4 O2 C8 . . . . -9.1(4) ?
C3 C4 O2 C8 . . . . 170.4(2) ?
