##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
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# Full details of the Crystallographic Information File format               #
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# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     'SHELXL97'
_journal_date_recd_electronic     2010-08-06
_journal_date_accepted     2010-08-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      9
_journal_page_first     m1182
_journal_page_last     m1182
_journal_paper_category     QM
_journal_coeditor_code     ZS2057
_publ_contact_author_name     'Dr. Peihua Zhu'
_publ_contact_author_address
;
School of Chemistry and Chemical Engineering
University of Jinan
Jinan 250022
People's Republic of China;
;
_publ_contact_author_email     chm_zhuph@ujn.edu.cn
_publ_contact_author_phone     '86 531 82765969'
_publ_section_title
;
Bis{1-[(o-tolyl)iminomethyl]-2-naphtholato}copper(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'Peihua Zhu'
;
 School of Chemistry and Chemical Engineering
 University of Jinan
 Jinan 250022
 People's Republic of China;
;
    'Jiemei Yu'
;
 School of Chemistry and Chemical Engineering
 University of Jinan
 Jinan 250022
 People's Republic of China;
;
    'Hongyan Wang'
;
 School of Chemistry and Chemical Engineering
 University of Jinan
 Jinan 250022
 People's Republic of China;
;
    'Chunlai Zhang'
;
 School of Chemistry and Chemical Engineering
 University of Jinan
 Jinan 250022
 People's Republic of China;
;
    'Qin Wei'
;
 School of Chemistry and Chemical Engineering
 University of Jinan
 Jinan 250022
 People's Republic of China;
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
Bis{1-[(o-tolyl)iminomethyl]-2-naphtholato}copper(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C36 H28 Cu N2 O2'
_chemical_formula_sum     'C36 H28 Cu N2 O2'
_chemical_formula_iupac     '[Cu (C18 H14 N O)2]'
_chemical_formula_weight     584.14
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     7.39342(16)
_cell_length_b     22.0666(5)
_cell_length_c     8.74653(19)
_cell_angle_alpha     90.00
_cell_angle_beta     95.775(2)
_cell_angle_gamma     90.00
_cell_volume     1419.73(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3786
_cell_measurement_theta_min     2.9131
_cell_measurement_theta_max     28.8613
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.19
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.366
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     606
_exptl_absorpt_coefficient_mu     0.805
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.8621
_exptl_absorpt_correction_T_max     0.8956
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7361
_diffrn_reflns_av_R_equivalents     0.0233
_diffrn_reflns_av_sigmaI/netI     0.0394
_diffrn_reflns_theta_min     2.92
_diffrn_reflns_theta_max     26.37
_diffrn_reflns_theta_full     26.37
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -27
_diffrn_reflns_limit_k_max     26
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2882
_reflns_number_gt     2058
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0568
_refine_ls_R_factor_gt     0.0374
_refine_ls_wR_factor_gt     0.0941
_refine_ls_wR_factor_ref     0.0984
_refine_ls_goodness_of_fit_ref     1.048
_refine_ls_restrained_S_all     1.048
_refine_ls_number_reflns     2882
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                'calc w=1/[σ²(Fo²)+(0.0550P)²+] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.565
_refine_diff_density_min     -1.036
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Cu' 'Cu' 0.3201 1.2651
                         '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'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2001)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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
    C C1 0.2037(3) 0.50730(10) -0.2657(3) 0.02945(14) Uani d . 1 . .
    H H1 0.2543 0.5301 -0.3401 0.035 Uiso calc R 1 . .
    C C2 0.1929(3) 0.44372(10) -0.2912(3) 0.02945(14) Uani d . 1 . .
    C C3 0.1469(3) 0.40463(10) -0.1721(2) 0.02945(14) Uani d . 1 . .
    C C4 0.1653(4) 0.34085(11) -0.1907(3) 0.0421(6) Uani d . 1 . .
    H H4 0.1347 0.3151 -0.1132 0.051 Uiso calc R 1 . .
    C C5 0.2260(4) 0.31703(11) -0.3183(3) 0.0435(6) Uani d . 1 . .
    H H5 0.2372 0.2752 -0.3259 0.052 Uiso calc R 1 . .
    C C6 0.2735(3) 0.35406(11) -0.4415(3) 0.0356(5) Uani d . 1 . .
    C C7 0.3357(4) 0.32855(12) -0.5738(3) 0.0445(6) Uani d . 1 . .
    H H7 0.3507 0.2868 -0.5792 0.053 Uiso calc R 1 . .
    C C8 0.3746(4) 0.36357(13) -0.6944(3) 0.0505(7) Uani d . 1 . .
    H H8 0.4166 0.3461 -0.7809 0.061 Uiso calc R 1 . .
    C C9 0.3505(4) 0.42579(13) -0.6864(3) 0.0461(7) Uani d . 1 . .
    H H9 0.3744 0.4498 -0.7693 0.055 Uiso calc R 1 . .
    C C10 0.2922(3) 0.45262(12) -0.5584(3) 0.0388(6) Uani d . 1 . .
    H H10 0.2783 0.4945 -0.5560 0.047 Uiso calc R 1 . .
    C C11 0.2529(3) 0.41766(10) -0.4298(2) 0.0302(5) Uani d . 1 . .
    C C12 0.1859(3) 0.60096(10) -0.1439(3) 0.0303(5) Uani d . 1 . .
    C C13 0.1197(3) 0.63778(11) -0.2651(3) 0.0378(6) Uani d . 1 . .
    H H13 0.0541 0.6209 -0.3510 0.045 Uiso calc R 1 . .
    C C14 0.1508(4) 0.69953(12) -0.2586(3) 0.0508(7) Uani d . 1 . .
    H H14 0.1067 0.7241 -0.3403 0.061 Uiso calc R 1 . .
    C C15 0.2467(4) 0.72443(12) -0.1319(4) 0.0545(8) Uani d . 1 . .
    H H15 0.2672 0.7660 -0.1272 0.065 Uiso calc R 1 . .
    C C16 0.3128(4) 0.68777(12) -0.0114(3) 0.0476(7) Uani d . 1 . .
    H H16 0.3790 0.7051 0.0736 0.057 Uiso calc R 1 . .
    C C17 0.2832(3) 0.62580(10) -0.0135(3) 0.0351(6) Uani d . 1 . .
    C C18 0.3561(4) 0.58665(14) 0.1189(3) 0.0566(8) Uani d . 1 . .
    H H18B 0.2568 0.5702 0.1683 0.085 Uiso calc R 1 . .
    H H18C 0.4319 0.6106 0.1913 0.085 Uiso calc R 1 . .
    H H18A 0.4263 0.5542 0.0819 0.085 Uiso calc R 1 . .
    Cu Cu1 0.0000 0.5000 0.0000 0.02945(14) Uani d S 1 . .
    N N1 0.1508(2) 0.53716(8) -0.1497(2) 0.02945(14) Uani d . 1 . .
    O O1 0.0924(2) 0.42288(7) -0.04412(16) 0.02945(14) Uani d . 1 . .
_geom_special_details
;
 All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    C1 N1 . 1.303(3) ?
    C1 C2 . 1.422(3) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.420(3) ?
    C2 C11 . 1.452(3) ?
    C3 O1 . 1.292(2) ?
    C3 C4 . 1.425(3) ?
    C4 C5 . 1.351(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.424(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.406(3) ?
    C6 C11 . 1.417(3) ?
    C7 C8 . 1.361(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.387(4) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.374(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.417(3) ?
    C10 H10 . 0.9300 ?
    C12 C13 . 1.385(3) ?
    C12 C17 . 1.398(3) ?
    C12 N1 . 1.432(3) ?
    C13 C14 . 1.382(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.369(4) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.379(4) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.385(3) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.501(4) ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
    C18 H18A . 0.9600 ?
    Cu1 O1 3_565 1.8881(15) ?
    Cu1 O1 . 1.8881(15) ?
    Cu1 N1 . 1.9804(17) ?
    Cu1 N1 3_565 1.9804(17) ?
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
    N1 C1 C2 . . 127.2(2) ?
    N1 C1 H1 . . 116.4 ?
    C2 C1 H1 . . 116.4 ?
    C3 C2 C1 . . 119.9(2) ?
    C3 C2 C11 . . 119.2(2) ?
    C1 C2 C11 . . 120.33(19) ?
    O1 C3 C2 . . 124.4(2) ?
    O1 C3 C4 . . 116.62(19) ?
    C2 C3 C4 . . 119.0(2) ?
    C5 C4 C3 . . 121.4(2) ?
    C5 C4 H4 . . 119.3 ?
    C3 C4 H4 . . 119.3 ?
    C4 C5 C6 . . 122.0(2) ?
    C4 C5 H5 . . 119.0 ?
    C6 C5 H5 . . 119.0 ?
    C7 C6 C11 . . 120.2(2) ?
    C7 C6 C5 . . 121.3(2) ?
    C11 C6 C5 . . 118.5(2) ?
    C8 C7 C6 . . 121.5(2) ?
    C8 C7 H7 . . 119.2 ?
    C6 C7 H7 . . 119.2 ?
    C7 C8 C9 . . 119.0(2) ?
    C7 C8 H8 . . 120.5 ?
    C9 C8 H8 . . 120.5 ?
    C10 C9 C8 . . 121.4(2) ?
    C10 C9 H9 . . 119.3 ?
    C8 C9 H9 . . 119.3 ?
    C9 C10 C11 . . 121.2(2) ?
    C9 C10 H10 . . 119.4 ?
    C11 C10 H10 . . 119.4 ?
    C6 C11 C10 . . 116.8(2) ?
    C6 C11 C2 . . 119.8(2) ?
    C10 C11 C2 . . 123.5(2) ?
    C13 C12 C17 . . 120.5(2) ?
    C13 C12 N1 . . 120.1(2) ?
    C17 C12 N1 . . 119.4(2) ?
    C14 C13 C12 . . 120.2(2) ?
    C14 C13 H13 . . 119.9 ?
    C12 C13 H13 . . 119.9 ?
    C15 C14 C13 . . 120.0(3) ?
    C15 C14 H14 . . 120.0 ?
    C13 C14 H14 . . 120.0 ?
    C14 C15 C16 . . 119.9(3) ?
    C14 C15 H15 . . 120.1 ?
    C16 C15 H15 . . 120.1 ?
    C15 C16 C17 . . 121.7(3) ?
    C15 C16 H16 . . 119.2 ?
    C17 C16 H16 . . 119.1 ?
    C16 C17 C12 . . 117.8(2) ?
    C16 C17 C18 . . 120.9(2) ?
    C12 C17 C18 . . 121.3(2) ?
    C17 C18 H18B . . 109.5 ?
    C17 C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C17 C18 H18A . . 109.5 ?
    H18B C18 H18A . . 109.5 ?
    H18C C18 H18A . . 109.5 ?
    O1 Cu1 O1 3_565 . 180.0 ?
    O1 Cu1 N1 3_565 . 90.07(7) ?
    O1 Cu1 N1 . . 89.93(7) ?
    O1 Cu1 N1 3_565 3_565 89.93(7) ?
    O1 Cu1 N1 . 3_565 90.07(7) ?
    N1 Cu1 N1 . 3_565 180.00(9) ?
    C1 N1 C12 . . 117.21(18) ?
    C1 N1 Cu1 . . 122.60(15) ?
    C12 N1 Cu1 . . 119.73(13) ?
    C3 O1 Cu1 . . 127.52(14) ?
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
    N1 C1 C2 C3 . . . . -10.7(4) ?
    N1 C1 C2 C11 . . . . 178.0(2) ?
    C1 C2 C3 O1 . . . . 8.4(3) ?
    C11 C2 C3 O1 . . . . 179.9(2) ?
    C1 C2 C3 C4 . . . . -170.0(2) ?
    C11 C2 C3 C4 . . . . 1.5(3) ?
    O1 C3 C4 C5 . . . . -178.2(2) ?
    C2 C3 C4 C5 . . . . 0.3(4) ?
    C3 C4 C5 C6 . . . . -0.5(4) ?
    C4 C5 C6 C7 . . . . -179.7(2) ?
    C4 C5 C6 C11 . . . . -1.1(4) ?
    C11 C6 C7 C8 . . . . -1.1(4) ?
    C5 C6 C7 C8 . . . . 177.4(3) ?
    C6 C7 C8 C9 . . . . -0.5(4) ?
    C7 C8 C9 C10 . . . . 1.4(4) ?
    C8 C9 C10 C11 . . . . -0.5(4) ?
    C7 C6 C11 C10 . . . . 1.9(3) ?
    C5 C6 C11 C10 . . . . -176.7(2) ?
    C7 C6 C11 C2 . . . . -178.5(2) ?
    C5 C6 C11 C2 . . . . 2.9(3) ?
    C9 C10 C11 C6 . . . . -1.1(3) ?
    C9 C10 C11 C2 . . . . 179.3(2) ?
    C3 C2 C11 C6 . . . . -3.1(3) ?
    C1 C2 C11 C6 . . . . 168.3(2) ?
    C3 C2 C11 C10 . . . . 176.4(2) ?
    C1 C2 C11 C10 . . . . -12.2(3) ?
    C17 C12 C13 C14 . . . . 0.6(4) ?
    N1 C12 C13 C14 . . . . 178.9(2) ?
    C12 C13 C14 C15 . . . . -0.3(4) ?
    C13 C14 C15 C16 . . . . 0.4(4) ?
    C14 C15 C16 C17 . . . . -0.8(4) ?
    C15 C16 C17 C12 . . . . 1.0(4) ?
    C15 C16 C17 C18 . . . . -179.9(2) ?
    C13 C12 C17 C16 . . . . -0.9(3) ?
    N1 C12 C17 C16 . . . . -179.3(2) ?
    C13 C12 C17 C18 . . . . -180.0(2) ?
    N1 C12 C17 C18 . . . . 1.7(3) ?
    C2 C1 N1 C12 . . . . 176.2(2) ?
    C2 C1 N1 Cu1 . . . . -11.6(3) ?
    C13 C12 N1 C1 . . . . 57.1(3) ?
    C17 C12 N1 C1 . . . . -124.5(2) ?
    C13 C12 N1 Cu1 . . . . -115.3(2) ?
    C17 C12 N1 Cu1 . . . . 63.1(2) ?
    O1 Cu1 N1 C1 3_565 . . . -154.08(18) ?
    O1 Cu1 N1 C1 . . . . 25.92(18) ?
    O1 Cu1 N1 C12 3_565 . . . 17.91(16) ?
    O1 Cu1 N1 C12 . . . . -162.09(16) ?
    C2 C3 O1 Cu1 . . . . 17.7(3) ?
    C4 C3 O1 Cu1 . . . . -163.90(16) ?
    N1 Cu1 O1 C3 . . . . -29.77(18) ?
    N1 Cu1 O1 C3 3_565 . . . 150.23(18) ?

