#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/01/2220172.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_2220172
loop_
_publ_author_name
'Xia, Rong'
'Xu, Hai-Jun'
'Wang, Han'
_publ_section_title
;
 Bis{2-[(2-cyanophenyl)iminomethyl]phenolato}copper(II)
;
_journal_coeditor_code           GW2050
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1539
_journal_paper_doi               10.1107/S160053680803417X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Cu (C14 H9 N2 O)2]'
_chemical_formula_moiety         'C28 H18 Cu N4 O2'
_chemical_formula_sum            'C28 H18 Cu N4 O2'
_chemical_formula_weight         506.00
_chemical_name_systematic
;
Bis{2-[(2-cyanophenyl)iminomethyl]phenolato}copper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 107.570(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.698(3)
_cell_length_b                   11.403(3)
_cell_length_c                   10.889(3)
_cell_measurement_reflns_used    2373
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3910
_cell_measurement_theta_min      3.0450
_cell_volume                     1148.0(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       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  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11307
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         3.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.986
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.1500
_exptl_crystal_size_mid          0.1000
_exptl_crystal_size_min          0.1000
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.429
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0503
_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)+(0.0516P)²+0.2943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1248
_reflns_number_gt                1952
_reflns_number_total             2629
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gw2050.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220172
_cod_database_fobs_code          2220172
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'
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
Cu Cu1 1.0000 0.5000 0.0000 0.03878(18) Uani d S 1
N N1 0.9612(2) 0.6674(2) 0.0368(2) 0.0383(5) Uani d . 1
O O1 1.0810(2) 0.46983(18) 0.1778(2) 0.0469(5) Uani d . 1
C C8 0.8569(3) 0.7359(3) -0.0563(3) 0.0400(6) Uani d . 1
C C1 1.1420(3) 0.6686(3) 0.2473(3) 0.0416(7) Uani d . 1
C C7 1.0377(3) 0.7214(3) 0.1397(3) 0.0416(7) Uani d . 1
H H7A 1.0234 0.8018 0.1439 0.050 Uiso calc R 1
C C9 0.7154(3) 0.6925(3) -0.1043(3) 0.0469(7) Uani d . 1
C C2 1.1568(3) 0.5450(3) 0.2631(3) 0.0403(7) Uani d . 1
C C4 1.3310(4) 0.5785(3) 0.4717(3) 0.0587(9) Uani d . 1
H H4A 1.3938 0.5479 0.5471 0.070 Uiso calc R 1
C C6 1.2221(3) 0.7432(3) 0.3469(3) 0.0535(8) Uani d . 1
H H6A 1.2098 0.8239 0.3373 0.064 Uiso calc R 1
C C13 0.8922(4) 0.8413(3) -0.1019(3) 0.0507(8) Uani d . 1
H H13A 0.9852 0.8715 -0.0698 0.061 Uiso calc R 1
C C14 0.6811(3) 0.5801(3) -0.0602(3) 0.0539(8) Uani d . 1
C C10 0.6108(4) 0.7564(4) -0.1967(3) 0.0624(10) Uani d . 1
H H10A 0.5162 0.7291 -0.2270 0.075 Uiso calc R 1
C C12 0.7880(5) 0.9012(3) -0.1957(4) 0.0670(10) Uani d . 1
H H12A 0.8126 0.9711 -0.2280 0.080 Uiso calc R 1
C C5 1.3176(4) 0.6996(3) 0.4574(3) 0.0601(9) Uani d . 1
H H5A 1.3720 0.7496 0.5211 0.072 Uiso calc R 1
C C3 1.2547(4) 0.5035(3) 0.3782(3) 0.0507(8) Uani d . 1
H H3A 1.2678 0.4231 0.3909 0.061 Uiso calc R 1
N N2 0.6591(4) 0.4905(3) -0.0242(4) 0.0716(9) Uani d . 1
C C11 0.6491(5) 0.8599(4) -0.2422(4) 0.0729(12) Uani d . 1
H H11A 0.5805 0.9021 -0.3049 0.087 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 Cu1 O1 3_765 . 180.00(12)
O1 Cu1 N1 3_765 3_765 90.78(9)
O1 Cu1 N1 . 3_765 89.22(9)
O1 Cu1 N1 3_765 . 89.22(9)
O1 Cu1 N1 . . 90.78(9)
N1 Cu1 N1 3_765 . 180.00(13)
C7 N1 C8 . . 116.8(2)
C7 N1 Cu1 . . 122.03(19)
C8 N1 Cu1 . . 120.84(18)
C2 O1 Cu1 . . 125.24(19)
C13 C8 C9 . . 119.5(3)
C13 C8 N1 . . 122.1(3)
C9 C8 N1 . . 118.4(3)
C2 C1 C6 . . 119.5(3)
C2 C1 C7 . . 122.5(3)
C6 C1 C7 . . 117.7(3)
N1 C7 C1 . . 125.9(3)
N1 C7 H7A . . 117.1
C1 C7 H7A . . 117.1
C8 C9 C10 . . 120.0(3)
C8 C9 C14 . . 119.1(3)
C10 C9 C14 . . 120.8(3)
O1 C2 C3 . . 119.6(3)
O1 C2 C1 . . 123.2(3)
C3 C2 C1 . . 117.2(3)
C3 C4 C5 . . 121.9(3)
C3 C4 H4A . . 119.1
C5 C4 H4A . . 119.1
C5 C6 C1 . . 121.7(3)
C5 C6 H6A . . 119.2
C1 C6 H6A . . 119.2
C8 C13 C12 . . 119.4(3)
C8 C13 H13A . . 120.3
C12 C13 H13A . . 120.3
N2 C14 C9 . . 177.6(4)
C11 C10 C9 . . 119.4(3)
C11 C10 H10A . . 120.3
C9 C10 H10A . . 120.3
C11 C12 C13 . . 121.3(4)
C11 C12 H12A . . 119.3
C13 C12 H12A . . 119.3
C6 C5 C4 . . 118.3(3)
C6 C5 H5A . . 120.9
C4 C5 H5A . . 120.9
C4 C3 C2 . . 121.5(3)
C4 C3 H3A . . 119.3
C2 C3 H3A . . 119.3
C12 C11 C10 . . 120.3(3)
C12 C11 H11A . . 119.9
C10 C11 H11A . . 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 O1 3_765 1.888(2)
Cu1 O1 . 1.888(2)
Cu1 N1 3_765 2.009(2)
Cu1 N1 . 2.009(2)
N1 C7 . 1.298(3)
N1 C8 . 1.429(3)
O1 C2 . 1.313(4)
C8 C13 . 1.382(4)
C8 C9 . 1.403(4)
C1 C2 . 1.421(4)
C1 C6 . 1.413(4)
C1 C7 . 1.429(4)
C7 H7A . 0.9300
C9 C10 . 1.398(4)
C9 C14 . 1.443(5)
C2 C3 . 1.407(4)
C4 C3 . 1.364(4)
C4 C5 . 1.391(5)
C4 H4A . 0.9300
C6 C5 . 1.371(4)
C6 H6A . 0.9300
C13 C12 . 1.381(4)
C13 H13A . 0.9300
C14 N2 . 1.137(4)
C10 C11 . 1.374(5)
C10 H10A . 0.9300
C12 C11 . 1.372(5)
C12 H12A . 0.9300
C5 H5A . 0.9300
C3 H3A . 0.9300
C11 H11A . 0.9300
