##############################################################################
###                                                                        ###
###        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.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# 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  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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# This file may be used for bona fide research purposes within the           #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
[1,1'-Diphenyl-3,3'-(propane-1,3-diyldinitrilo)dibut-1-enolato]copper(II)
;
_chemical_name_common     '1384 Amir M3'
_chemical_formula_moiety     'C23 H24 Cu N2 O2'
_chemical_formula_sum     'C23 H24 Cu N2 O2'
_chemical_formula_iupac     '[Cu (C23 H24 N2 O2)]'
_chemical_formula_weight     423.98
_chemical_melting_point     ?
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
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'
_cell_length_a     12.2047(12)
_cell_length_b     20.320(2)
_cell_length_c     8.9992(9)
_cell_angle_alpha     90.00
_cell_angle_beta     117.4050(10)
_cell_angle_gamma     90.00
_cell_volume     1981.3(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8926
_cell_measurement_theta_min     2.13
_cell_measurement_theta_max     30.02
_cell_measurement_temperature     100(2)
_exptl_crystal_description     oval
_exptl_crystal_colour     black
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.46
_exptl_crystal_size_min     0.35
_exptl_crystal_density_diffrn     1.421
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     884
_exptl_absorpt_coefficient_mu     1.123
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.57
_exptl_absorpt_correction_T_max     0.68
_exptl_special_details
;
Dark crystals from methanol. Bruker Kappa APEXII CCD diffractometer, full
sphere data collection.
;
_diffrn_ambient_temperature     100(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'
_diffrn_measurement_method     'φ and ω'
_diffrn_reflns_number     11028
_diffrn_reflns_av_R_equivalents     0.0194
_diffrn_reflns_av_sigmaI/netI     0.0148
_diffrn_reflns_theta_min     2.57
_diffrn_reflns_theta_max     29.99
_diffrn_reflns_theta_full     29.99
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -28
_diffrn_reflns_limit_k_max     28
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_decay_%     0
_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     2881
_reflns_number_gt     2780
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0232
_refine_ls_R_factor_gt     0.0223
_refine_ls_wR_factor_gt     0.0619
_refine_ls_wR_factor_ref     0.0627
_refine_ls_goodness_of_fit_ref     1.051
_refine_ls_restrained_S_all     1.051
_refine_ls_number_reflns     2881
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0348P)²+1.3062P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.418
_refine_diff_density_min     -0.344
_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'
    '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'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_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
    Cu Cu1 0.5000 0.285854(8) 0.2500 0.01604(6) Uani d S 1 . .
    O O1 0.58573(7) 0.35237(3) 0.19375(9) 0.01910(14) Uani d . 1 . .
    N N1 0.62650(9) 0.21952(4) 0.30042(11) 0.01918(16) Uani d . 1 . .
    C C1 0.62862(9) 0.44403(5) -0.00488(13) 0.02073(18) Uani d . 1 . .
    H H1A 0.5465 0.4414 -0.0198 0.025 Uiso calc R 1 . .
    C C2 0.66276(10) 0.49606(5) -0.07553(14) 0.0239(2) Uani d . 1 . .
    H H2A 0.6036 0.5284 -0.1396 0.029 Uiso calc R 1 . .
    C C3 0.78315(10) 0.50085(5) -0.05262(13) 0.0227(2) Uani d . 1 . .
    H H3A 0.8060 0.5360 -0.1023 0.027 Uiso calc R 1 . .
    C C4 0.87007(10) 0.45401(5) 0.04322(13) 0.02263(19) Uani d . 1 . .
    H H4A 0.9529 0.4578 0.0615 0.027 Uiso calc R 1 . .
    C C5 0.83576(9) 0.40168(5) 0.11223(13) 0.02040(18) Uani d . 1 . .
    H H5A 0.8954 0.3696 0.1767 0.024 Uiso calc R 1 . .
    C C6 0.71452(9) 0.39567(5) 0.08789(12) 0.01713(17) Uani d . 1 . .
    C C7 0.67614(9) 0.33962(5) 0.16071(11) 0.01684(17) Uani d . 1 . .
    C C8 0.73853(9) 0.28017(5) 0.18784(13) 0.01919(18) Uani d . 1 . .
    H H8A 0.8005 0.2772 0.1522 0.023 Uiso calc R 1 . .
    C C9 0.71826(10) 0.22321(5) 0.26408(12) 0.01902(18) Uani d . 1 . .
    C C10 0.81019(10) 0.16754(5) 0.30347(14) 0.0251(2) Uani d . 1 . .
    H H10A 0.7658 0.1263 0.2580 0.038 Uiso calc R 1 . .
    H H10B 0.8598 0.1635 0.4250 0.038 Uiso calc R 1 . .
    H H10C 0.8645 0.1768 0.2528 0.038 Uiso calc R 1 . .
    C C11 0.60558(11) 0.16066(5) 0.37870(13) 0.02317(19) Uani d . 1 . .
    H H11A 0.5853 0.1741 0.4689 0.028 Uiso calc R 1 . .
    H H11B 0.6821 0.1341 0.4297 0.028 Uiso calc R 1 . .
    C C12 0.5000 0.11873(7) 0.2500 0.0241(3) Uani d S 1 . .
    H H12A 0.4673 0.0900 0.3093 0.029 Uiso calc PR 0.50 . .
    H H12B 0.5327 0.0900 0.1907 0.029 Uiso calc PR 0.50 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cu1 0.01768(9) 0.01421(9) 0.01729(9) 0.000 0.00895(7) 0.000
    O1 0.0193(3) 0.0171(3) 0.0243(3) 0.0005(2) 0.0130(3) 0.0002(2)
    N1 0.0227(4) 0.0162(4) 0.0171(4) 0.0019(3) 0.0078(3) 0.0007(3)
    C1 0.0175(4) 0.0200(4) 0.0242(5) -0.0008(3) 0.0093(4) -0.0006(3)
    C2 0.0222(5) 0.0208(4) 0.0254(5) -0.0008(4) 0.0083(4) 0.0019(4)
    C3 0.0244(5) 0.0227(5) 0.0208(4) -0.0068(4) 0.0103(4) -0.0020(3)
    C4 0.0192(4) 0.0275(5) 0.0225(4) -0.0055(4) 0.0108(4) -0.0029(4)
    C5 0.0159(4) 0.0240(5) 0.0207(4) -0.0014(3) 0.0079(4) -0.0008(3)
    C6 0.0164(4) 0.0185(4) 0.0164(4) -0.0019(3) 0.0075(3) -0.0028(3)
    C7 0.0156(4) 0.0184(4) 0.0156(4) -0.0014(3) 0.0064(3) -0.0026(3)
    C8 0.0174(4) 0.0194(4) 0.0205(4) 0.0005(3) 0.0085(4) -0.0031(3)
    C9 0.0193(4) 0.0175(4) 0.0161(4) 0.0020(3) 0.0046(4) -0.0033(3)
    C10 0.0238(5) 0.0208(5) 0.0260(5) 0.0065(4) 0.0075(4) -0.0027(4)
    C11 0.0308(5) 0.0183(4) 0.0199(4) 0.0031(4) 0.0113(4) 0.0039(3)
    C12 0.0327(8) 0.0159(6) 0.0260(7) 0.000 0.0154(6) 0.000
_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
    Cu1 O1 . 1.9145(7) ?
    Cu1 O1 2_655 1.9145(7) ?
    Cu1 N1 . 1.9394(9) ?
    Cu1 N1 2_655 1.9395(9) ?
    O1 C7 . 1.2943(11) ?
    N1 C9 . 1.3054(14) ?
    N1 C11 . 1.4688(13) ?
    C1 C2 . 1.3925(14) ?
    C1 C6 . 1.3986(14) ?
    C1 H1A . 0.9500 ?
    C2 C3 . 1.3900(15) ?
    C2 H2A . 0.9500 ?
    C3 C4 . 1.3903(16) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.3896(14) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.3978(13) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.4928(13) ?
    C7 C8 . 1.3882(13) ?
    C8 C9 . 1.4241(14) ?
    C8 H8A . 0.9500 ?
    C9 C10 . 1.5158(14) ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 C12 . 1.5342(14) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 C11 2_655 1.5342(14) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
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_655 90.19(4) ?
    O1 Cu1 N1 . . 94.56(3) ?
    O1 Cu1 N1 2_655 . 154.41(4) ?
    O1 Cu1 N1 . 2_655 154.41(4) ?
    O1 Cu1 N1 2_655 2_655 94.56(3) ?
    N1 Cu1 N1 . 2_655 91.94(5) ?
    C7 O1 Cu1 . . 123.15(6) ?
    C9 N1 C11 . . 121.70(9) ?
    C9 N1 Cu1 . . 125.72(7) ?
    C11 N1 Cu1 . . 112.51(7) ?
    C2 C1 C6 . . 120.42(9) ?
    C2 C1 H1A . . 119.8 ?
    C6 C1 H1A . . 119.8 ?
    C3 C2 C1 . . 120.23(10) ?
    C3 C2 H2A . . 119.9 ?
    C1 C2 H2A . . 119.9 ?
    C2 C3 C4 . . 119.78(10) ?
    C2 C3 H3A . . 120.1 ?
    C4 C3 H3A . . 120.1 ?
    C5 C4 C3 . . 120.01(10) ?
    C5 C4 H4A . . 120.0 ?
    C3 C4 H4A . . 120.0 ?
    C4 C5 C6 . . 120.79(10) ?
    C4 C5 H5A . . 119.6 ?
    C6 C5 H5A . . 119.6 ?
    C5 C6 C1 . . 118.73(9) ?
    C5 C6 C7 . . 121.42(9) ?
    C1 C6 C7 . . 119.84(9) ?
    O1 C7 C8 . . 126.18(9) ?
    O1 C7 C6 . . 114.90(8) ?
    C8 C7 C6 . . 118.91(9) ?
    C7 C8 C9 . . 126.09(9) ?
    C7 C8 H8A . . 117.0 ?
    C9 C8 H8A . . 117.0 ?
    N1 C9 C8 . . 121.79(9) ?
    N1 C9 C10 . . 121.77(9) ?
    C8 C9 C10 . . 116.43(9) ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C9 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    N1 C11 C12 . . 111.17(8) ?
    N1 C11 H11A . . 109.4 ?
    C12 C11 H11A . . 109.4 ?
    N1 C11 H11B . . 109.4 ?
    C12 C11 H11B . . 109.4 ?
    H11A C11 H11B . . 108.0 ?
    C11 C12 C11 . 2_655 112.54(12) ?
    C11 C12 H12A . . 109.1 ?
    C11 C12 H12A 2_655 . 109.1 ?
    C11 C12 H12B . . 109.1 ?
    C11 C12 H12B 2_655 . 109.1 ?
    H12A C12 H12B . . 107.8 ?
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 C7 2_655 . . . 171.40(9) ?
    N1 Cu1 O1 C7 . . . . 16.58(8) ?
    N1 Cu1 O1 C7 2_655 . . . -87.60(11) ?
    O1 Cu1 N1 C9 . . . . -12.71(9) ?
    O1 Cu1 N1 C9 2_655 . . . -112.72(10) ?
    N1 Cu1 N1 C9 2_655 . . . 142.51(10) ?
    O1 Cu1 N1 C11 . . . . 170.40(7) ?
    O1 Cu1 N1 C11 2_655 . . . 70.39(11) ?
    N1 Cu1 N1 C11 2_655 . . . -34.37(6) ?
    C6 C1 C2 C3 . . . . -0.83(16) ?
    C1 C2 C3 C4 . . . . -0.93(16) ?
    C2 C3 C4 C5 . . . . 1.64(16) ?
    C3 C4 C5 C6 . . . . -0.59(15) ?
    C4 C5 C6 C1 . . . . -1.15(15) ?
    C4 C5 C6 C7 . . . . 179.79(9) ?
    C2 C1 C6 C5 . . . . 1.85(15) ?
    C2 C1 C6 C7 . . . . -179.07(9) ?
    Cu1 O1 C7 C8 . . . . -11.84(13) ?
    Cu1 O1 C7 C6 . . . . 168.64(6) ?
    C5 C6 C7 O1 . . . . 151.44(9) ?
    C1 C6 C7 O1 . . . . -27.61(13) ?
    C5 C6 C7 C8 . . . . -28.11(13) ?
    C1 C6 C7 C8 . . . . 152.83(9) ?
    O1 C7 C8 C9 . . . . -3.07(16) ?
    C6 C7 C8 C9 . . . . 176.44(9) ?
    C11 N1 C9 C8 . . . . 179.86(9) ?
    Cu1 N1 C9 C8 . . . . 3.24(14) ?
    C11 N1 C9 C10 . . . . -1.20(15) ?
    Cu1 N1 C9 C10 . . . . -177.83(7) ?
    C7 C8 C9 N1 . . . . 7.75(16) ?
    C7 C8 C9 C10 . . . . -171.24(10) ?
    C9 N1 C11 C12 . . . . -102.55(11) ?
    Cu1 N1 C11 C12 . . . . 74.48(9) ?
    N1 C11 C12 C11 . . . 2_655 -37.68(6) ?
data_global
_journal_date_recd_electronic     2009-01-04
_journal_date_accepted     2009-01-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      2
_journal_page_first     m196
_journal_page_last     m196
_journal_paper_category     QM
_journal_coeditor_code     DN2424
_publ_contact_author_name     'Mehdi Amirnasr'
_publ_contact_author_address
;
Department of Chemistry
Isfahan University of Technology
Isfahan 84156-83111
Iran
;
_publ_contact_author_email     amirnasr@cc.iut.ac.ir
_publ_contact_author_fax     '98 311 3912350'
_publ_contact_author_phone     '98 311 3912351'
_publ_section_title
;
[1,1'-Diphenyl-3,3'-(propane-1,3-diyldinitrilo)dibut-1-enolato]copper(II)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Salehi, Mehdi' .
;
Department of Chemistry
Isfahan University of Technology
Isfahan 84156-83111
Iran
;
    'Meghdadi, Soraia' .
;
Department of Chemistry
Isfahan University of Technology
Isfahan 84156-83111
Iran
;
    'Amirnasr, Mehdi' .
;
Department of Chemistry
Isfahan University of Technology
Isfahan 84156-83111
Iran
;
    'Mereiter, Kurt' .
;
Faculty of Chemistry,
Vienna University of Technology, Getreidemarkt 9/164SC,
A-1060 Vienna,
Austria
;
_publ_section_synopsis     .
