#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:40:45 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179857 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/53/7015346.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_7015346
loop_
_publ_author_name
'Kopylovich, Maximilian N.'
'Nunes, Andreia C. C.'
'Mahmudov, Kamran T.'
'Haukka, Matti'
'Mac Leod, Tatiana C. O.'
'Martins, Luísa M D R S'
'Kuznetsov, Maxim L.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Complexes of copper(II) with 3-(ortho-substituted
 phenylhydrazo)pentane-2,4-diones: syntheses, properties and catalytic
 activity for cyclohexane oxidation.
;
_journal_issue                   12
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2822
_journal_page_last               2836
_journal_paper_doi               10.1039/c0dt01527j
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C12 H10 Cu N2 O4'
_chemical_formula_sum            'C12 H10 Cu N2 O4'
_chemical_formula_weight         309.76
_chemical_name_systematic
;
?
;
_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                 90.281(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5658(13)
_cell_length_b                   5.2797(6)
_cell_length_c                   18.662(2)
_cell_measurement_reflns_used    2335
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.60
_cell_measurement_theta_min      2.80
_cell_volume                     1139.6(2)
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_molecular_graphics    'Diamond v.3.2c (Brandenburg, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2008 (Burla et al., 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device       '62mm x 62mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II DUO CCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  'curved graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6932
_diffrn_reflns_theta_full        25.85
_diffrn_reflns_theta_max         25.85
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    1.928
_exptl_absorpt_correction_T_max  0.8768
_exptl_absorpt_correction_T_min  0.3622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.909
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0441
_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)+(0.0888P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1378
_reflns_number_gt                1450
_reflns_number_total             2149
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt01527j.txt
_cod_data_source_block           13
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7015346
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.36747(4) 0.25656(10) 0.24626(3) 0.0168(2) Uani 1 1 d . . .
O4 O 0.0182(3) 0.9310(7) 0.18190(18) 0.0315(9) Uani 1 1 d . . .
O5 O 0.2820(3) 0.5311(6) 0.28437(16) 0.0202(7) Uani 1 1 d . . .
O6 O 0.4422(3) 0.2241(6) 0.34490(16) 0.0207(7) Uani 1 1 d . . .
O7 O 0.4531(3) -0.0324(6) 0.22212(15) 0.0205(7) Uani 1 1 d . . .
N1 N 0.2904(3) 0.2817(7) 0.15330(19) 0.0140(8) Uani 1 1 d . . .
N2 N 0.2074(3) 0.4400(7) 0.13892(18) 0.0167(8) Uani 1 1 d . . .
C1 C 0.3984(3) -0.0737(9) 0.0978(2) 0.0156(9) Uani 1 1 d . . .
C2 C 0.4153(4) -0.2303(8) 0.0376(2) 0.0182(10) Uani 1 1 d . . .
H2 H 0.4686 -0.3666 0.0412 0.022 Uiso 1 1 calc R . .
C3 C 0.3583(4) -0.1938(9) -0.0254(2) 0.0198(10) Uani 1 1 d . . .
H3 H 0.3707 -0.3043 -0.0648 0.024 Uiso 1 1 calc R . .
C4 C 0.2814(4) 0.0077(9) -0.0313(2) 0.0208(10) Uani 1 1 d . . .
H4 H 0.2428 0.0391 -0.0755 0.025 Uiso 1 1 calc R . .
C5 C 0.2611(4) 0.1626(9) 0.0273(2) 0.0199(10) Uani 1 1 d . . .
H5 H 0.2082 0.2994 0.0226 0.024 Uiso 1 1 calc R . .
C6 C 0.3162(3) 0.1230(9) 0.0928(2) 0.0166(10) Uani 1 1 d . . .
C7 C 0.1659(4) 0.6157(9) 0.1836(2) 0.0157(9) Uani 1 1 d . . .
C8 C 0.0696(4) 0.7636(9) 0.1494(2) 0.0202(10) Uani 1 1 d . . .
C9 C 0.0361(4) 0.6987(10) 0.0744(3) 0.0280(12) Uani 1 1 d . . .
H9A H -0.0267 0.8104 0.0585 0.042 Uiso 1 1 calc R . .
H9B H 0.0101 0.5222 0.0723 0.042 Uiso 1 1 calc R . .
H9C H 0.1030 0.7208 0.0429 0.042 Uiso 1 1 calc R . .
C10 C 0.2058(4) 0.6637(9) 0.2553(2) 0.0162(10) Uani 1 1 d . . .
C11 C 0.1618(4) 0.8781(9) 0.2995(2) 0.0202(10) Uani 1 1 d . . .
H11A H 0.0839 0.8380 0.3167 0.030 Uiso 1 1 calc R . .
H11B H 0.1589 1.0323 0.2703 0.030 Uiso 1 1 calc R . .
H11C H 0.2135 0.9050 0.3406 0.030 Uiso 1 1 calc R . .
C12 C 0.4723(4) -0.1315(9) 0.1610(2) 0.0193(10) Uani 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 Cu1 O5 171.76(13) . . yes
O7 Cu1 N1 94.65(13) . . yes
O5 Cu1 N1 92.57(14) . . yes
O7 Cu1 O6 85.78(12) . . yes
O5 Cu1 O6 86.85(13) . . yes
N1 Cu1 O6 177.77(13) . . ?
O7 Cu1 O7 88.86(6) . 2_655 ?
O5 Cu1 O7 90.25(12) . 2_655 ?
N1 Cu1 O7 124.85(13) . 2_655 ?
O6 Cu1 O7 57.32(11) . 2_655 ?
C10 O5 Cu1 129.4(3) . . ?
C12 O6 Cu1 101.6(3) 2_655 . ?
C12 O7 Cu1 130.0(3) . . ?
C12 O7 Cu1 82.9(3) . 2_645 ?
Cu1 O7 Cu1 140.12(15) . 2_645 ?
N2 N1 C6 111.6(3) . . ?
N2 N1 Cu1 124.1(3) . . ?
C6 N1 Cu1 124.3(3) . . ?
N1 N2 C7 125.7(4) . . ?
C2 C1 C6 118.4(4) . . ?
C2 C1 C12 115.6(4) . . ?
C6 C1 C12 126.1(4) . . ?
C3 C2 C1 122.6(4) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 119.0(4) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 118.3(4) . . ?
C5 C6 N1 120.5(4) . . ?
C1 C6 N1 121.3(4) . . ?
N2 C7 C10 126.1(4) . . ?
N2 C7 C8 111.3(4) . . ?
C10 C7 C8 122.6(4) . . ?
O4 C8 C9 120.4(4) . . ?
O4 C8 C7 121.7(4) . . ?
C9 C8 C7 118.0(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O5 C10 C7 122.0(4) . . ?
O5 C10 C11 115.3(4) . . ?
C7 C10 C11 122.7(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O6 C12 O7 118.0(4) 2_645 . ?
O6 C12 C1 120.4(4) 2_645 . ?
O7 C12 C1 121.6(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O7 1.875(3) . yes
Cu1 O5 1.895(3) . yes
Cu1 N1 1.951(4) . yes
Cu1 O6 2.037(3) . yes
Cu1 O7 2.426(3) 2_655 ?
O4 C8 1.227(5) . yes
O5 C10 1.248(5) . yes
O6 C12 1.254(6) 2_655 ?
O7 C12 1.275(5) . yes
O7 Cu1 2.426(3) 2_645 ?
N1 N2 1.300(5) . yes
N1 C6 1.438(6) . yes
N2 C7 1.338(6) . yes
C1 C2 1.409(6) . ?
C1 C6 1.411(6) . ?
C1 C12 1.485(6) . ?
C2 C3 1.359(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(6) . ?
C5 H5 0.9500 . ?
C7 C10 1.435(6) . ?
C7 C8 1.500(6) . ?
C8 C9 1.491(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.492(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O6 1.254(6) 2_645 ?
