#------------------------------------------------------------------------------
#$Date: 2016-08-07 12:29:29 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185566 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/55/7055561.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_7055561
loop_
_publ_author_name
'Novoa, Néstor'
'Roisnel, Thierry'
'Dorcet, Vincent'
'Cador, Olivier'
'Manzur, Carolina'
'Carrillo, David'
'Hamon, Jean-René'
_publ_section_title
;
 Efficient preparation of multimetallic ONO-based Schiff base complexes of
 nickel(ii) and copper(ii)
;
_journal_issue                   7
_journal_name_full               'New J. Chem.'
_journal_page_first              5920
_journal_paper_doi               10.1039/C6NJ00932H
_journal_volume                  40
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H19 Cu N2 O3'
_chemical_formula_sum            'C22 H19 Cu N2 O3'
_chemical_formula_weight         422.93
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2016-03-04 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.720(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6780(15)
_cell_length_b                   19.302(4)
_cell_length_c                   11.5537(16)
_cell_measurement_reflns_used    1719
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.52
_cell_measurement_theta_min      2.67
_cell_measurement_wavelength     0.71073
_cell_volume                     1832.9(6)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'CRYSCALc (T. Roisnel, local program, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1682
_diffrn_reflns_av_unetI/netI     0.2702
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11382
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.437
_diffrn_reflns_theta_min         3.256
_exptl_absorpt_coefficient_mu    1.218
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       board
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.917
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.2134
_refine_ls_R_factor_gt           0.0818
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0611P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1858
_reflns_number_gt                1801
_reflns_number_total             4161
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6nj00932h2.cif
_cod_data_source_block           NN132
_cod_depositor_comments
'Adding full bibliography for 7055559--7055562.cif.'
_cod_database_code               7055561
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cu1 Cu 0.50306(11) 0.07051(5) 0.07240(7) 0.0196(3) Uani 1 1 d . .
N1 N 0.3867(7) 0.1261(3) -0.0694(4) 0.0182(14) Uani 1 1 d . .
N2 N 0.6748(7) 0.0323(3) 0.2252(5) 0.0172(14) Uani 1 1 d . .
O1 O 0.6320(6) 0.0401(3) -0.0274(4) 0.0231(13) Uani 1 1 d . .
O2 O 0.3775(6) 0.1049(3) 0.1700(4) 0.0223(13) Uani 1 1 d . .
C1 C 0.6055(8) 0.0812(4) -0.1255(5) 0.0187(18) Uani 1 1 d . .
C6 C 0.7035(8) 0.0780(4) -0.2016(6) 0.0248(19) Uani 1 1 d . .
H2 H 0.7902 0.0455 -0.1844 0.030 Uiso 1 1 calc R U
C5 C 0.6747(9) 0.1218(4) -0.3017(6) 0.027(2) Uani 1 1 d . .
H3 H 0.7406 0.1185 -0.3532 0.032 Uiso 1 1 calc R U
C4 C 0.5494(9) 0.1709(4) -0.3275(6) 0.029(2) Uani 1 1 d . .
H4 H 0.5306 0.2012 -0.3954 0.035 Uiso 1 1 calc R U
C3 C 0.4528(8) 0.1746(4) -0.2520(6) 0.0234(19) Uani 1 1 d . .
H5 H 0.3712 0.2093 -0.2666 0.028 Uiso 1 1 calc R U
C2 C 0.4735(8) 0.1284(4) -0.1554(6) 0.0165(17) Uani 1 1 d . .
C7 C 0.2323(8) 0.1449(4) -0.0940(6) 0.0166(17) Uani 1 1 d . .
C8 C 0.1242(8) 0.1654(4) -0.2200(6) 0.0198(18) Uani 1 1 d . .
H8A H 0.1497 0.2130 -0.2376 0.030 Uiso 1 1 calc R U
H8B H 0.0100 0.1628 -0.2236 0.030 Uiso 1 1 calc R U
H8C H 0.1427 0.1339 -0.2807 0.030 Uiso 1 1 calc R U
C9 C 0.1599(9) 0.1464(4) -0.0014(6) 0.0194(18) Uani 1 1 d . .
H9 H 0.0485 0.1595 -0.0260 0.023 Uiso 1 1 calc R U
C10 C 0.2317(9) 0.1310(4) 0.1229(6) 0.0200(18) Uani 1 1 d . .
C11 C 0.1432(9) 0.1452(4) 0.2120(6) 0.0177(17) Uani 1 1 d . .
C12 C -0.0227(8) 0.1620(4) 0.1754(6) 0.0189(18) Uani 1 1 d . .
H12 H -0.0833 0.1612 0.0908 0.023 Uiso 1 1 calc R U
C13 C -0.1019(9) 0.1799(4) 0.2586(6) 0.0223(19) Uani 1 1 d . .
H13 H -0.2133 0.1930 0.2312 0.027 Uiso 1 1 calc R U
C14 C -0.0148(9) 0.1781(4) 0.3821(6) 0.0238(19) Uani 1 1 d . .
C15 C 0.1484(9) 0.1602(4) 0.4226(6) 0.0221(19) Uani 1 1 d . .
H15 H 0.2058 0.1582 0.5078 0.027 Uiso 1 1 calc R U
C16 C 0.2283(9) 0.1452(4) 0.3383(6) 0.0232(19) Uani 1 1 d . .
H16 H 0.3414 0.1349 0.3664 0.028 Uiso 1 1 calc R U
O3 O -0.0791(6) 0.1935(3) 0.4746(4) 0.0274(14) Uani 1 1 d . .
C17 C -0.2417(9) 0.2197(4) 0.4367(6) 0.028(2) Uani 1 1 d . .
H18A H -0.2490 0.2604 0.3845 0.042 Uiso 1 1 calc R U
H18B H -0.2714 0.2328 0.5088 0.042 Uiso 1 1 calc R U
H18C H -0.3164 0.1838 0.3909 0.042 Uiso 1 1 calc R U
C18 C 0.6494(9) 0.0306(4) 0.3361(6) 0.0230(19) Uani 1 1 d . .
H19 H 0.5432 0.0394 0.3394 0.028 Uiso 1 1 calc R U
C19 C 0.7722(9) 0.0165(4) 0.4425(6) 0.024(2) Uani 1 1 d . .
H20 H 0.7489 0.0144 0.5173 0.029 Uiso 1 1 calc R U
C20 C 0.9299(8) 0.0053(4) 0.4425(5) 0.0181(17) Uani 1 1 d . .
C21 C 0.9538(8) 0.0036(4) 0.3288(6) 0.0194(18) Uani 1 1 d . .
H22 H 1.0584 -0.0068 0.3235 0.023 Uiso 1 1 calc R U
C22 C 0.8245(9) 0.0169(4) 0.2227(6) 0.0193(18) Uani 1 1 d . .
H23 H 0.8431 0.0150 0.1460 0.023 Uiso 1 1 calc R U
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
_geom_angle_site_symmetry_3
O2 Cu1 O1 177.4(2) .
O2 Cu1 N1 93.7(2) .
O1 Cu1 N1 84.8(2) .
O2 Cu1 N2 90.7(2) .
O1 Cu1 N2 90.2(2) .
N1 Cu1 N2 163.9(2) .
O2 Cu1 O1 96.00(19) 3_655
O1 Cu1 O1 86.37(19) 3_655
N1 Cu1 O1 102.8(2) 3_655
N2 Cu1 O1 92.1(2) 3_655
C7 N1 C2 124.4(6) .
C7 N1 Cu1 123.1(4) .
C2 N1 Cu1 110.8(4) .
C22 N2 C18 117.5(6) .
C22 N2 Cu1 120.2(4) .
C18 N2 Cu1 121.6(5) .
C1 O1 Cu1 110.4(4) .
C1 O1 Cu1 113.7(4) 3_655
Cu1 O1 Cu1 93.63(19) 3_655
C10 O2 Cu1 123.0(4) .
O1 C1 C6 121.8(6) .
O1 C1 C2 119.5(6) .
C6 C1 C2 118.7(6) .
C5 C6 C1 120.7(7) .
C5 C6 H2 119.7 .
C1 C6 H2 119.7 .
C6 C5 C4 120.6(6) .
C6 C5 H3 119.7 .
C4 C5 H3 119.7 .
C3 C4 C5 119.0(7) .
C3 C4 H4 120.5 .
C5 C4 H4 120.5 .
C4 C3 C2 121.3(7) .
C4 C3 H5 119.4 .
C2 C3 H5 119.4 .
C3 C2 C1 119.5(6) .
C3 C2 N1 128.0(7) .
C1 C2 N1 112.1(6) .
N1 C7 C9 120.6(6) .
N1 C7 C8 123.4(6) .
C9 C7 C8 116.0(6) .
C7 C8 H8A 109.5 .
C7 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
C7 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
C10 C9 C7 128.0(7) .
C10 C9 H9 116.0 .
C7 C9 H9 116.0 .
O2 C10 C9 124.1(6) .
O2 C10 C11 115.2(6) .
C9 C10 C11 120.6(7) .
C12 C11 C16 117.3(6) .
C12 C11 C10 122.7(6) .
C16 C11 C10 120.0(6) .
C13 C12 C11 122.4(6) .
C13 C12 H12 118.8 .
C11 C12 H12 118.8 .
C14 C13 C12 118.5(7) .
C14 C13 H13 120.7 .
C12 C13 H13 120.7 .
C15 C14 C13 121.1(6) .
C15 C14 O3 114.4(6) .
C13 C14 O3 124.5(7) .
C14 C15 C16 119.9(7) .
C14 C15 H15 120.0 .
C16 C15 H15 120.0 .
C15 C16 C11 120.7(7) .
C15 C16 H16 119.7 .
C11 C16 H16 119.7 .
C14 O3 C17 116.2(5) .
O3 C17 H18A 109.5 .
O3 C17 H18B 109.5 .
H18A C17 H18B 109.5 .
O3 C17 H18C 109.5 .
H18A C17 H18C 109.5 .
H18B C17 H18C 109.5 .
N2 C18 C19 122.1(6) .
N2 C18 H19 118.9 .
C19 C18 H19 118.9 .
C18 C19 C20 120.9(6) .
C18 C19 H20 119.5 .
C20 C19 H20 119.5 .
C19 C20 C21 116.7(6) .
C19 C20 C20 122.8(7) 3_756
C21 C20 C20 120.5(8) 3_756
C22 C21 C20 120.2(6) .
C22 C21 H22 119.9 .
C20 C21 H22 119.9 .
N2 C22 C21 122.2(6) .
N2 C22 H23 118.9 .
C21 C22 H23 118.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.920(4) .
Cu1 O1 1.937(4) .
Cu1 N1 1.948(5) .
Cu1 N2 2.047(5) .
Cu1 O1 2.410(5) 3_655
N1 C7 1.328(8) .
N1 C2 1.428(8) .
N2 C22 1.342(8) .
N2 C18 1.369(7) .
O1 C1 1.342(8) .
O1 Cu1 2.410(5) 3_655
O2 C10 1.307(8) .
C1 C6 1.407(8) .
C1 C2 1.416(9) .
C6 C5 1.390(10) .
C6 H2 0.9500 .
C5 C4 1.400(10) .
C5 H3 0.9500 .
C4 C3 1.392(9) .
C4 H4 0.9500 .
C3 C2 1.395(9) .
C3 H5 0.9500 .
C7 C9 1.404(8) .
C7 C8 1.510(9) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.401(9) .
C9 H9 0.9500 .
C10 C11 1.494(9) .
C11 C12 1.403(9) .
C11 C16 1.408(9) .
C12 C13 1.392(9) .
C12 H12 0.9500 .
C13 C14 1.384(9) .
C13 H13 0.9500 .
C14 C15 1.384(10) .
C14 O3 1.388(8) .
C15 C16 1.396(9) .
C15 H15 0.9500 .
C16 H16 0.9500 .
O3 C17 1.428(8) .
C17 H18A 0.9800 .
C17 H18B 0.9800 .
C17 H18C 0.9800 .
C18 C19 1.372(9) .
C18 H19 0.9500 .
C19 C20 1.385(9) .
C19 H20 0.9500 .
C20 C21 1.395(9) .
C20 C20 1.500(12) 3_756
C21 C22 1.394(9) .
C21 H22 0.9500 .
C22 H23 0.9500 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
Cu1 O1 C1 C6 169.0(5) . .
Cu1 O1 C1 C6 -87.3(7) 3_655 .
Cu1 O1 C1 C2 -12.3(8) . .
Cu1 O1 C1 C2 91.4(7) 3_655 .
O1 C1 C6 C5 -179.2(7) . .
C2 C1 C6 C5 2.2(11) . .
C1 C6 C5 C4 1.1(12) . .
C6 C5 C4 C3 -0.7(12) . .
C5 C4 C3 C2 -3.1(11) . .
C4 C3 C2 C1 6.5(11) . .
C4 C3 C2 N1 178.9(7) . .
O1 C1 C2 C3 175.4(6) . .
C6 C1 C2 C3 -5.9(10) . .
O1 C1 C2 N1 1.8(9) . .
C6 C1 C2 N1 -179.5(6) . .
C7 N1 C2 C3 31.4(12) . .
Cu1 N1 C2 C3 -163.3(6) . .
C7 N1 C2 C1 -155.7(7) . .
Cu1 N1 C2 C1 9.6(7) . .
C2 N1 C7 C9 -174.8(7) . .
Cu1 N1 C7 C9 21.7(10) . .
C2 N1 C7 C8 5.4(11) . .
Cu1 N1 C7 C8 -158.1(5) . .
N1 C7 C9 C10 1.2(13) . .
C8 C7 C9 C10 -179.0(7) . .
Cu1 O2 C10 C9 -9.8(10) . .
Cu1 O2 C10 C11 171.2(5) . .
C7 C9 C10 O2 -7.9(13) . .
C7 C9 C10 C11 171.1(7) . .
O2 C10 C11 C12 -169.0(7) . .
C9 C10 C11 C12 11.9(11) . .
O2 C10 C11 C16 14.1(10) . .
C9 C10 C11 C16 -164.9(7) . .
C16 C11 C12 C13 1.5(11) . .
C10 C11 C12 C13 -175.4(7) . .
C11 C12 C13 C14 -2.7(12) . .
C12 C13 C14 C15 1.2(12) . .
C12 C13 C14 O3 -178.9(7) . .
C13 C14 C15 C16 1.5(12) . .
O3 C14 C15 C16 -178.4(7) . .
C14 C15 C16 C11 -2.7(12) . .
C12 C11 C16 C15 1.2(11) . .
C10 C11 C16 C15 178.2(7) . .
C15 C14 O3 C17 173.3(7) . .
C13 C14 O3 C17 -6.6(11) . .
C22 N2 C18 C19 2.6(11) . .
Cu1 N2 C18 C19 -168.6(6) . .
N2 C18 C19 C20 1.9(13) . .
C18 C19 C20 C21 -5.0(11) . .
C18 C19 C20 C20 175.6(9) . 3_756
C19 C20 C21 C22 3.8(11) . .
C20 C20 C21 C22 -176.8(8) 3_756 .
C18 N2 C22 C21 -3.8(11) . .
Cu1 N2 C22 C21 167.5(6) . .
C20 C21 C22 N2 0.6(11) . .
