#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/77/2227756.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227756
loop_
_publ_author_name
'Zhu, Peihua'
'Wang, Hongyan'
'Wang, Yan'
'Chen, Yanli'
'Wei, Qin'
_publ_section_title
;
 Bis{1-[(4-methylphenyl)iminomethyl]-2-naphtholato-κ²N,O}copper(II)
;
_journal_coeditor_code           LH5095
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1076
_journal_paper_doi               10.1107/S1600536810030667
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Cu (C18 H14 N O)2]'
_chemical_formula_moiety         'C36 H28 Cu N2 O2'
_chemical_formula_sum            'C36 H28 Cu N2 O2'
_chemical_formula_weight         584.14
_chemical_name_systematic
;
Bis{1-[(4-methylphenyl)iminomethyl]-2-naphtholato-
κ²N,O}copper(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.559(7)
_cell_angle_beta                 98.728(7)
_cell_angle_gamma                102.573(7)
_cell_formula_units_Z            1
_cell_length_a                   7.0948(6)
_cell_length_b                   10.2335(7)
_cell_length_c                   10.5784(10)
_cell_measurement_reflns_used    1252
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.942
_cell_measurement_theta_min      2.525
_cell_volume                     708.01(11)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7213
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  0.9164
_exptl_absorpt_correction_T_min  0.8237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             303
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2878
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0320
_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)+(0.0431P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0761
_reflns_number_gt                2395
_reflns_number_total             2878
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5095.cif
_cod_data_source_block           I
_cod_original_cell_volume        708.01(10)
_cod_database_code               2227756
_cod_database_fobs_code          2227756
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.0000 0.0000 0.03685(13) Uani d S 1 . .
O O 0.63653(18) -0.08439(14) 0.10934(13) 0.0465(3) Uani d . 1 . .
N N 0.3572(2) 0.06231(15) 0.14161(14) 0.0353(3) Uani d . 1 . .
C C 0.2582(3) 0.17043(18) 0.14181(17) 0.0348(4) Uani d . 1 . .
C C1 0.3384(3) 0.00334(19) 0.23682(18) 0.0374(4) Uani d . 1 . .
H H1 0.2561 0.0326 0.2922 0.045 Uiso calc R 1 . .
C C2 0.5826(3) -0.13173(18) 0.20525(18) 0.0380(4) Uani d . 1 . .
C C5 0.0594(3) 0.14665(19) 0.14435(19) 0.0403(4) Uani d . 1 . .
H H5 -0.0138 0.0584 0.1419 0.048 Uiso calc R 1 . .
C C6 -0.0300(3) 0.2550(2) 0.15063(19) 0.0464(5) Uani d . 1 . .
H H6 -0.1636 0.2380 0.1525 0.056 Uiso calc R 1 . .
C C7 0.3611(3) 0.30083(19) 0.13974(19) 0.0443(5) Uani d . 1 . .
H H7 0.4929 0.3167 0.1332 0.053 Uiso calc R 1 . .
C C8 0.3767(3) -0.16156(19) 0.37004(18) 0.0397(4) Uani d . 1 . .
C C9 0.0726(3) 0.3872(2) 0.15411(19) 0.0459(5) Uani d . 1 . .
C C10 0.4283(3) -0.09993(19) 0.26615(18) 0.0366(4) Uani d . 1 . .
C C12 0.2192(3) -0.1408(2) 0.43269(19) 0.0481(5) Uani d . 1 . .
H H12 0.1454 -0.0824 0.4091 0.058 Uiso calc R 1 . .
C C14 0.4870(3) -0.24967(19) 0.41041(19) 0.0452(5) Uani d . 1 . .
C C15 0.2694(3) 0.4076(2) 0.1473(2) 0.0493(5) Uani d . 1 . .
H H15 0.3417 0.4952 0.1478 0.059 Uiso calc R 1 . .
C C17 -0.0240(4) 0.5069(2) 0.1698(3) 0.0680(7) Uani d . 1 . .
H H17A -0.1612 0.4714 0.1253 0.102 Uiso calc R 1 . .
H H17B 0.0411 0.5744 0.1308 0.102 Uiso calc R 1 . .
H H17C -0.0132 0.5507 0.2631 0.102 Uiso calc R 1 . .
C C18 0.6458(3) -0.2737(2) 0.3493(2) 0.0530(5) Uani d . 1 . .
H H18 0.7205 -0.3293 0.3779 0.064 Uiso calc R 1 . .
C C19 0.1725(3) -0.2047(2) 0.5277(2) 0.0595(6) Uani d . 1 . .
H H19 0.0684 -0.1889 0.5678 0.071 Uiso calc R 1 . .
C C20 0.6920(3) -0.2190(2) 0.2516(2) 0.0493(5) Uani d . 1 . .
H H20 0.7966 -0.2380 0.2136 0.059 Uiso calc R 1 . .
C C21 0.2798(4) -0.2931(2) 0.5642(2) 0.0651(6) Uani d . 1 . .
H H21 0.2455 -0.3379 0.6270 0.078 Uiso calc R 1 . .
C C23 0.4339(4) -0.3138(2) 0.5084(2) 0.0602(6) Uani d . 1 . .
H H23 0.5067 -0.3714 0.5350 0.072 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'
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'
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
O Cu1 O 2_655 . 180 y
O Cu1 N 2_655 . 89.58(5) y
O Cu1 N . . 90.42(5) y
O Cu1 N 2_655 2_655 90.42(5) ?
O Cu1 N . 2_655 89.58(5) ?
N Cu1 N . 2_655 180 y
C2 O Cu1 . . 128.62(11) n
C1 N C . . 115.44(14) n
C1 N Cu1 . . 122.54(12) n
C N Cu1 . . 121.94(11) n
C7 C C5 . . 118.92(16) n
C7 C N . . 120.13(15) n
C5 C N . . 120.95(16) n
N C1 C10 . . 127.97(17) n
N C1 H1 . . 116.0 ?
C10 C1 H1 . . 116.0 ?
O C2 C10 . . 124.11(16) ?
O C2 C20 . . 116.69(16) ?
C10 C2 C20 . . 119.19(17) ?
C C5 C6 . . 119.60(17) ?
C C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C9 C6 C5 . . 122.15(17) ?
C9 C6 H6 . . 118.9 ?
C5 C6 H6 . . 118.9 ?
C15 C7 C . . 120.38(17) ?
C15 C7 H7 . . 119.8 ?
C C7 H7 . . 119.8 ?
C12 C8 C14 . . 117.34(17) ?
C12 C8 C10 . . 123.66(17) ?
C14 C8 C10 . . 118.99(17) ?
C6 C9 C15 . . 117.32(17) ?
C6 C9 C17 . . 121.49(18) ?
C15 C9 C17 . . 121.16(19) ?
C2 C10 C1 . . 120.13(16) ?
C2 C10 C8 . . 119.57(16) ?
C1 C10 C8 . . 119.94(16) ?
C19 C12 C8 . . 121.51(19) ?
C19 C12 H12 . . 119.2 ?
C8 C12 H12 . . 119.2 ?
C23 C14 C8 . . 119.42(19) ?
C23 C14 C18 . . 121.54(18) ?
C8 C14 C18 . . 119.03(18) ?
C7 C15 C9 . . 121.53(18) ?
C7 C15 H15 . . 119.2 ?
C9 C15 H15 . . 119.2 ?
C9 C17 H17A . . 109.5 ?
C9 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C9 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C20 C18 C14 . . 122.24(18) ?
C20 C18 H18 . . 118.9 ?
C14 C18 H18 . . 118.9 ?
C12 C19 C21 . . 120.4(2) ?
C12 C19 H19 . . 119.8 ?
C21 C19 H19 . . 119.8 ?
C18 C20 C2 . . 120.91(19) ?
C18 C20 H20 . . 119.5 ?
C2 C20 H20 . . 119.5 ?
C23 C21 C19 . . 120.0(2) ?
C23 C21 H21 . . 120.0 ?
C19 C21 H21 . . 120.0 ?
C21 C23 C14 . . 121.4(2) ?
C21 C23 H23 . . 119.3 ?
C14 C23 H23 . . 119.3 ?
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 O 2_655 1.8837(12) ?
Cu1 O . 1.8837(12) y
Cu1 N . 1.9848(14) y
Cu1 N 2_655 1.9848(14) ?
O C2 . 1.302(2) n
N C1 . 1.307(2) n
N C . 1.434(2) n
C C7 . 1.382(2) ?
C C5 . 1.384(2) ?
C1 C10 . 1.420(2) n
C1 H1 . 0.9300 ?
C2 C10 . 1.408(2) n
C2 C20 . 1.431(2) ?
C5 C6 . 1.385(2) ?
C5 H5 . 0.9300 ?
C6 C9 . 1.378(3) ?
C6 H6 . 0.9300 ?
C7 C15 . 1.380(2) ?
C7 H7 . 0.9300 ?
C8 C12 . 1.411(3) ?
C8 C14 . 1.417(3) ?
C8 C10 . 1.452(3) ?
C9 C15 . 1.382(3) ?
C9 C17 . 1.515(2) ?
C12 C19 . 1.373(3) ?
C12 H12 . 0.9300 ?
C14 C23 . 1.414(3) ?
C14 C18 . 1.417(3) ?
C15 H15 . 0.9300 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 C20 . 1.343(3) ?
C18 H18 . 0.9300 ?
C19 C21 . 1.390(3) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C21 C23 . 1.350(3) ?
C21 H21 . 0.9300 ?
C23 H23 . 0.9300 ?
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
O Cu1 O C2 2_655 . . . -7E1(10) ?
N Cu1 O C2 . . . . 25.66(16) ?
N Cu1 O C2 2_655 . . . -154.34(16) ?
O Cu1 N C1 2_655 . . . 159.10(14) ?
O Cu1 N C1 . . . . -20.90(14) ?
N Cu1 N C1 2_655 . . . -2E1(10) ?
O Cu1 N C 2_655 . . . -17.40(13) ?
O Cu1 N C . . . . 162.60(13) ?
N Cu1 N C 2_655 . . . 16E1(10) ?
C1 N C C7 . . . . 127.26(18) ?
Cu1 N C C7 . . . . -56.0(2) ?
C1 N C C5 . . . . -52.6(2) ?
Cu1 N C C5 . . . . 124.13(16) ?
C N C1 C10 . . . . -176.06(16) ?
Cu1 N C1 C10 . . . . 7.2(3) ?
Cu1 O C2 C10 . . . . -15.1(3) ?
Cu1 O C2 C20 . . . . 166.16(12) ?
C7 C C5 C6 . . . . -2.8(3) ?
N C C5 C6 . . . . 177.08(17) ?
C C5 C6 C9 . . . . 0.2(3) ?
C5 C C7 C15 . . . . 3.4(3) ?
N C C7 C15 . . . . -176.46(17) ?
C5 C6 C9 C15 . . . . 1.8(3) ?
C5 C6 C9 C17 . . . . -176.09(19) ?
O C2 C10 C1 . . . . -8.6(3) ?
C20 C2 C10 C1 . . . . 170.11(16) ?
O C2 C10 C8 . . . . 178.34(16) ?
C20 C2 C10 C8 . . . . -3.0(3) ?
N C1 C10 C2 . . . . 11.9(3) ?
N C1 C10 C8 . . . . -174.99(17) ?
C12 C8 C10 C2 . . . . -177.19(18) ?
C14 C8 C10 C2 . . . . 1.7(3) ?
C12 C8 C10 C1 . . . . 9.7(3) ?
C14 C8 C10 C1 . . . . -171.42(16) ?
C14 C8 C12 C19 . . . . -0.9(3) ?
C10 C8 C12 C19 . . . . 178.02(18) ?
C12 C8 C14 C23 . . . . 1.0(3) ?
C10 C8 C14 C23 . . . . -177.99(17) ?
C12 C8 C14 C18 . . . . 179.69(18) ?
C10 C8 C14 C18 . . . . 0.7(3) ?
C C7 C15 C9 . . . . -1.4(3) ?
C6 C9 C15 C7 . . . . -1.2(3) ?
C17 C9 C15 C7 . . . . 176.7(2) ?
C23 C14 C18 C20 . . . . 176.8(2) ?
C8 C14 C18 C20 . . . . -1.9(3) ?
C8 C12 C19 C21 . . . . -0.3(3) ?
C14 C18 C20 C2 . . . . 0.6(3) ?
O C2 C20 C18 . . . . -179.34(18) ?
C10 C2 C20 C18 . . . . 1.9(3) ?
C12 C19 C21 C23 . . . . 1.5(4) ?
C19 C21 C23 C14 . . . . -1.5(4) ?
C8 C14 C23 C21 . . . . 0.2(3) ?
C18 C14 C23 C21 . . . . -178.5(2) ?
