#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/98/2209865.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_2209865
loop_
_publ_author_name
'Arıcı, Cengiz'
_publ_section_title
'[N,N'-Bis(1-benzoylisopropylidene)propane-1,3-diamine(2{-})]copper(II)'
_journal_coeditor_code           HG2065
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1950
_journal_page_last               m1951
_journal_paper_doi               10.1107/S1600536806028315
_journal_volume                  62
_journal_year                    2006
_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         423.99
_chemical_name_systematic
'[N,N'-Bis(1-benzoylisopropylidene)propane-1,3-diamine(2-)]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                 102.113(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.2385(12)
_cell_length_b                   8.3306(13)
_cell_length_c                   20.1928(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.07
_cell_measurement_theta_min      10.78
_cell_volume                     3986.6(7)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1993)'
_computing_data_reduction        'CAD-4 EXPRESS'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4331
_diffrn_reflns_theta_full        26.81
_diffrn_reflns_theta_max         26.81
_diffrn_reflns_theta_min         2.59
_diffrn_standards_decay_%        0.028
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.116
_exptl_absorpt_correction_T_max  0.800
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'empirical via ψ scans (MolEN; Fair, 1990)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.364
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0654P)²+1.7129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                3509
_reflns_number_total             4228
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2065.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2209865
_cod_database_fobs_code          2209865
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
C C1 0.72630(8) 0.3766(2) 0.40599(10) 0.0369(4) Uani d . 1
C C2 0.69255(9) 0.3884(3) 0.45250(10) 0.0401(4) Uani d . 1
H H2 0.6582 0.3344 0.4434 0.048 Uiso calc R 1
C C3 0.70673(9) 0.4782(2) 0.51383(11) 0.0392(4) Uani d . 1
C C4 0.65857(11) 0.5121(3) 0.54835(13) 0.0540(6) Uani d . 1
H H4A 0.6721 0.5731 0.5888 0.081 Uiso calc R 1
H H4B 0.6429 0.4126 0.5598 0.081 Uiso calc R 1
H H4C 0.6300 0.5723 0.5184 0.081 Uiso calc R 1
C C5 0.76308(10) 0.6456(3) 0.59658(11) 0.0469(5) Uani d . 1
H H5A 0.7555 0.5865 0.6351 0.056 Uiso calc R 1
H H5B 0.7352 0.7303 0.5860 0.056 Uiso calc R 1
C C6 0.82064(11) 0.7198(3) 0.61565(12) 0.0523(6) Uani d . 1
H H6A 0.8202 0.8009 0.6500 0.063 Uiso calc R 1
H H6B 0.8290 0.7732 0.5762 0.063 Uiso calc R 1
C C7 0.86687(11) 0.6020(3) 0.64197(11) 0.0503(5) Uani d . 1
H H7A 0.9002 0.6598 0.6648 0.060 Uiso calc R 1
H H7B 0.8551 0.5322 0.6749 0.060 Uiso calc R 1
C C8 0.96884(11) 0.4361(4) 0.66733(12) 0.0624(7) Uani d . 1
H H8A 0.9515 0.4961 0.6981 0.094 Uiso calc R 1
H H8B 1.0037 0.4864 0.6637 0.094 Uiso calc R 1
H H8C 0.9761 0.3286 0.6839 0.094 Uiso calc R 1
C C9 0.92976(9) 0.4317(3) 0.59849(10) 0.0448(5) Uani d . 1
C C10 0.95053(9) 0.3472(3) 0.54806(11) 0.0499(5) Uani d . 1
H H10 0.9815 0.2803 0.5623 0.060 Uiso calc R 1
C C11 0.92857(9) 0.3564(3) 0.48007(11) 0.0454(5) Uani d . 1
C C12 0.95562(9) 0.2693(3) 0.43055(11) 0.0461(5) Uani d . 1
C C13 1.00884(11) 0.2011(4) 0.44794(13) 0.0620(7) Uani d . 1
H H13 1.0308 0.2190 0.4909 0.074 Uiso calc R 1
C C14 1.02979(12) 0.1071(4) 0.40263(15) 0.0703(8) Uani d . 1
H H14 1.0652 0.0600 0.4157 0.084 Uiso calc R 1
C C15 0.99884(13) 0.0830(4) 0.33891(15) 0.0679(7) Uani d . 1
H H15 1.0129 0.0186 0.3086 0.081 Uiso calc R 1
C C16 0.94642(13) 0.1547(4) 0.31936(13) 0.0673(7) Uani d . 1
H H16 0.9256 0.1406 0.2755 0.081 Uiso calc R 1
C C17 0.92501(10) 0.2474(4) 0.36513(12) 0.0549(6) Uani d . 1
H H17 0.8898 0.2954 0.3518 0.066 Uiso calc R 1
C C18 0.70409(9) 0.3082(2) 0.33691(10) 0.0392(4) Uani d . 1
C C19 0.74065(11) 0.2271(3) 0.30401(11) 0.0493(5) Uani d . 1
H H19 0.7785 0.2174 0.3250 0.059 Uiso calc R 1
C C20 0.72177(13) 0.1604(3) 0.24048(12) 0.0620(7) Uani d . 1
H H20 0.7466 0.1030 0.2201 0.074 Uiso calc R 1
C C21 0.66659(14) 0.1787(4) 0.20751(12) 0.0664(8) Uani d . 1
H H21 0.6539 0.1343 0.1648 0.080 Uiso calc R 1
C C22 0.63032(13) 0.2634(4) 0.23838(13) 0.0673(8) Uani d . 1
H H22 0.5931 0.2782 0.2158 0.081 Uiso calc R 1
C C23 0.64843(10) 0.3272(3) 0.30290(12) 0.0525(6) Uani d . 1
H H23 0.6232 0.3828 0.3233 0.063 Uiso calc R 1
N N1 0.75707(8) 0.5362(2) 0.53802(9) 0.0388(4) Uani d . 1
N N2 0.88097(8) 0.5040(2) 0.58728(9) 0.0413(4) Uani d . 1
O O1 0.77796(6) 0.4231(2) 0.41587(7) 0.0456(4) Uani d . 1
O O2 0.88330(7) 0.4344(3) 0.45414(8) 0.0589(5) Uani d . 1
Cu Cu 0.824123(10) 0.47615(3) 0.502480(11) 0.03686(10) 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
_geom_angle_publ_flag
O1 C1 C2 124.98(19) ?
O1 C1 C18 114.01(17) ?
C2 C1 C18 121.00(19) ?
C1 C2 C3 124.2(2) ?
C1 C2 H2 117.9 ?
C3 C2 H2 117.9 ?
N1 C3 C2 123.66(19) ?
N1 C3 C4 120.7(2) ?
C2 C3 C4 115.6(2) ?
C3 C4 H4A 109.5 ?
C3 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
C3 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
N1 C5 C6 112.97(18) ?
N1 C5 H5A 109.0 ?
C6 C5 H5A 109.0 ?
N1 C5 H5B 109.0 ?
C6 C5 H5B 109.0 ?
H5A C5 H5B 107.8 ?
C5 C6 C7 114.0(2) ?
C5 C6 H6A 108.8 ?
C7 C6 H6A 108.8 ?
C5 C6 H6B 108.8 ?
C7 C6 H6B 108.8 ?
H6A C6 H6B 107.7 ?
N2 C7 C6 111.79(18) ?
N2 C7 H7A 109.3 ?
C6 C7 H7A 109.3 ?
N2 C7 H7B 109.3 ?
C6 C7 H7B 109.3 ?
H7A C7 H7B 107.9 ?
C9 C8 H8A 109.5 ?
C9 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C9 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
N2 C9 C10 123.48(19) ?
N2 C9 C8 121.3(2) ?
C10 C9 C8 115.2(2) ?
C11 C10 C9 124.9(2) ?
C11 C10 H10 117.5 ?
C9 C10 H10 117.5 ?
O2 C11 C10 123.8(2) ?
O2 C11 C12 115.40(19) ?
C10 C11 C12 120.8(2) ?
C17 C12 C13 118.2(2) ?
C17 C12 C11 118.7(2) ?
C13 C12 C11 123.1(2) ?
C14 C13 C12 121.1(2) ?
C14 C13 H13 119.4 ?
C12 C13 H13 119.4 ?
C15 C14 C13 120.3(3) ?
C15 C14 H14 119.9 ?
C13 C14 H14 119.9 ?
C14 C15 C16 119.8(3) ?
C14 C15 H15 120.1 ?
C16 C15 H15 120.1 ?
C15 C16 C17 120.0(2) ?
C15 C16 H16 120.0 ?
C17 C16 H16 120.0 ?
C12 C17 C16 120.6(2) ?
C12 C17 H17 119.7 ?
C16 C17 H17 119.7 ?
C23 C18 C19 118.0(2) ?
C23 C18 C1 122.6(2) ?
C19 C18 C1 119.3(2) ?
C20 C19 C18 121.2(2) ?
C20 C19 H19 119.4 ?
C18 C19 H19 119.4 ?
C21 C20 C19 120.3(3) ?
C21 C20 H20 119.9 ?
C19 C20 H20 119.9 ?
C20 C21 C22 119.2(2) ?
C20 C21 H21 120.4 ?
C22 C21 H21 120.4 ?
C21 C22 C23 121.0(3) ?
C21 C22 H22 119.5 ?
C23 C22 H22 119.5 ?
C18 C23 C22 120.2(3) ?
C18 C23 H23 119.9 ?
C22 C23 H23 119.9 ?
C3 N1 C5 117.07(18) ?
C3 N1 Cu 123.04(14) ?
C5 N1 Cu 119.83(15) ?
C9 N2 C7 118.12(19) ?
C9 N2 Cu 122.61(15) ?
C7 N2 Cu 119.16(15) ?
C1 O1 Cu 124.98(13) ?
C11 O2 Cu 123.08(14) ?
O1 Cu O2 81.40(7) yes
O1 Cu N2 170.07(7) yes
O2 Cu N2 90.14(8) yes
O1 Cu N1 91.29(7) yes
O2 Cu N1 170.53(7) yes
N2 Cu N1 97.64(8) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.285(2) ?
C1 C2 1.372(3) ?
C1 C18 1.499(3) ?
C2 C3 1.426(3) ?
C2 H2 0.9300 ?
C3 N1 1.308(3) ?
C3 C4 1.507(3) ?
C4 H4A 0.9600 ?
C4 H4B 0.9600 ?
C4 H4C 0.9600 ?
C5 N1 1.476(3) ?
C5 C6 1.500(4) ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C6 C7 1.501(4) ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 N2 1.470(3) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 C9 1.509(3) ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
C9 N2 1.304(3) ?
C9 C10 1.415(3) ?
C10 C11 1.367(3) ?
C10 H10 0.9300 ?
C11 O2 1.288(3) ?
C11 C12 1.494(3) ?
C12 C17 1.385(3) ?
C12 C13 1.385(3) ?
C13 C14 1.380(4) ?
C13 H13 0.9300 ?
C14 C15 1.361(4) ?
C14 H14 0.9300 ?
C15 C16 1.384(4) ?
C15 H15 0.9300 ?
C16 C17 1.386(4) ?
C16 H16 0.9300 ?
C17 H17 0.9300 ?
C18 C23 1.388(3) ?
C18 C19 1.389(3) ?
C19 C20 1.385(3) ?
C19 H19 0.9300 ?
C20 C21 1.372(4) ?
C20 H20 0.9300 ?
C21 C22 1.374(5) ?
C21 H21 0.9300 ?
C22 C23 1.390(4) ?
C22 H22 0.9300 ?
C23 H23 0.9300 ?
N1 Cu 1.9740(18) yes
N2 Cu 1.9735(18) yes
O1 Cu 1.9196(15) yes
O2 Cu 1.9285(16) yes
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
O1 C1 C2 C3 11.2(3)
C18 C1 C2 C3 -167.75(18)
C1 C2 C3 N1 -12.1(3)
C1 C2 C3 C4 164.4(2)
N1 C5 C6 C7 -66.3(3)
C5 C6 C7 N2 74.8(3)
N2 C9 C10 C11 13.7(4)
C8 C9 C10 C11 -165.2(2)
C9 C10 C11 O2 -5.6(4)
C9 C10 C11 C12 176.5(2)
O2 C11 C12 C17 -14.4(3)
C10 C11 C12 C17 163.7(2)
O2 C11 C12 C13 169.4(3)
C10 C11 C12 C13 -12.6(4)
C17 C12 C13 C14 -3.3(4)
C11 C12 C13 C14 173.0(3)
C12 C13 C14 C15 1.8(5)
C13 C14 C15 C16 0.7(5)
C14 C15 C16 C17 -1.6(5)
C13 C12 C17 C16 2.4(4)
C11 C12 C17 C16 -174.0(3)
C15 C16 C17 C12 0.0(5)
O1 C1 C18 C23 -145.9(2)
C2 C1 C18 C23 33.2(3)
O1 C1 C18 C19 31.8(3)
C2 C1 C18 C19 -149.1(2)
C23 C18 C19 C20 -3.0(3)
C1 C18 C19 C20 179.3(2)
C18 C19 C20 C21 2.5(4)
C19 C20 C21 C22 -0.2(4)
C20 C21 C22 C23 -1.5(4)
C19 C18 C23 C22 1.3(4)
C1 C18 C23 C22 178.9(2)
C21 C22 C23 C18 1.0(4)
C2 C3 N1 C5 171.49(19)
C4 C3 N1 C5 -4.8(3)
C2 C3 N1 Cu -11.4(3)
C4 C3 N1 Cu 172.36(15)
C6 C5 N1 C3 -173.62(19)
C6 C5 N1 Cu 9.1(2)
C10 C9 N2 C7 -173.6(2)
C8 C9 N2 C7 5.2(3)
C10 C9 N2 Cu 10.2(3)
C8 C9 N2 Cu -171.01(19)
C6 C7 N2 C9 160.4(2)
C6 C7 N2 Cu -23.3(3)
C2 C1 O1 Cu 14.0(3)
C18 C1 O1 Cu -167.02(13)
C10 C11 O2 Cu -25.7(4)
C12 C11 O2 Cu 152.26(17)
C1 O1 Cu O2 159.05(19)
C1 O1 Cu N1 -27.00(18)
C11 O2 Cu O1 -138.4(2)
C11 O2 Cu N2 36.3(2)
C9 N2 Cu O2 -28.45(19)
C7 N2 Cu O2 155.42(17)
C9 N2 Cu N1 156.96(18)
C7 N2 Cu N1 -19.17(17)
C3 N1 Cu O1 25.35(16)
C5 N1 Cu O1 -157.58(15)
C3 N1 Cu N2 -150.31(16)
C5 N1 Cu N2 26.77(16)
