#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/07/2220761.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_2220761
loop_
_publ_author_name
'Salehi, Mehdi'
'Meghdadi, Soraia'
'Amirnasr, Mehdi'
'Mereiter, Kurt'
_publ_section_title
;
 [1,1'-Diphenyl-3,3'-(propane-1,3-diyldinitrilo)dibut-1-enolato]copper(II)
;
_journal_coeditor_code           DN2424
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m196
_journal_paper_doi               10.1107/S1600536809001081
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (C23 H24 N2 O2)]'
_chemical_formula_moiety         'C23 H24 Cu N2 O2'
_chemical_formula_sum            'C23 H24 Cu N2 O2'
_chemical_formula_weight         423.98
_chemical_name_common            '1384 Amir M3'
_chemical_name_systematic
;
[1,1'-Diphenyl-3,3'-(propane-1,3-diyldinitrilo)dibut-1-enolato]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                 117.4050(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2047(12)
_cell_length_b                   20.320(2)
_cell_length_c                   8.9992(9)
_cell_measurement_reflns_used    8926
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      2.13
_cell_volume                     1981.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11028
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.123
_exptl_absorpt_correction_T_max  0.68
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       oval
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.344
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0223
_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)+(0.0348P)²+1.3062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0627
_reflns_number_gt                2780
_reflns_number_total             2881
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2424.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2220761
_cod_database_fobs_code          2220761
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 0.5000 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_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_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_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_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) ?
