#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:45:59 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179346 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/43/4324318.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_4324318
loop_
_publ_author_name
'Maximilian N. Kopylovich'
'Kamran T. Mahmudov'
'M. Fátima C. Guedes da Silva'
'Paweł J. Figiel'
'Yauhen Yu. Karabach'
'Maxim L. Kuznetsov'
'Konstantin V. Luzyanin'
'Armando J. L. Pombeiro'
_publ_section_title
;
 Ortho-Hydroxyphenylhydrazo-β-Diketones: Tautomery, Coordination Ability,
 and Catalytic Activity of Their Copper(II) Complexes toward Oxidation of
 Cyclohexane and Benzylic Alcohols
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              918
_journal_page_last               931
_journal_paper_doi               10.1021/ic101516k
_journal_volume                  50
_journal_year                    2011
_chemical_formula_moiety         'C13 H15 Cu N5 O4'
_chemical_formula_sum            'C13 H15 Cu N5 O4'
_chemical_formula_weight         368.84
_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                 90.938(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8153(18)
_cell_length_b                   15.232(3)
_cell_length_c                   9.3858(16)
_cell_measurement_reflns_used    1543
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.65
_cell_measurement_theta_min      2.47
_cell_volume                     1403.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0722
_diffrn_reflns_av_sigmaI/netI    0.0784
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10718
_diffrn_reflns_theta_full        27.09
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    1.587
_exptl_absorpt_correction_T_max  0.8324
_exptl_absorpt_correction_T_min  0.5988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_description       prism
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0441
_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)+(0.0617P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                2134
_reflns_number_total             3074
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic101516k_si_002_12.cif
_cod_data_source_block           compound14
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4324318
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
C1 C 1.0069(4) 0.8179(3) 0.8189(4) 0.0141(8) Uani 1 1 d .
C2 C 0.9534(4) 0.7359(2) 0.8685(4) 0.0134(8) Uani 1 1 d .
C3 C 1.0013(4) 0.6568(2) 0.8141(4) 0.0155(9) Uani 1 1 d .
H3 H 0.9661 0.6040 0.8472 0.019 Uiso 1 1 calc R
C4 C 1.1006(4) 0.6559(3) 0.7118(4) 0.0187(9) Uani 1 1 d .
H4 H 1.1330 0.6032 0.6756 0.022 Uiso 1 1 calc R
C5 C 1.1508(4) 0.7353(3) 0.6642(4) 0.0138(8) Uani 1 1 d .
C6 C 1.1047(4) 0.8163(3) 0.7146(4) 0.0155(8) Uani 1 1 d .
H6 H 1.1394 0.8684 0.6784 0.019 Uiso 1 1 calc R
C11 C 0.5219(4) 0.7453(3) 1.2804(4) 0.0196(9) Uani 1 1 d .
H11A H 0.5522 0.7465 1.3781 0.029 Uiso 1 1 calc R
H11B H 0.4789 0.6900 1.2602 0.029 Uiso 1 1 calc R
H11C H 0.4578 0.7920 1.2638 0.029 Uiso 1 1 calc R
C12 C 0.6420(4) 0.7571(2) 1.1849(4) 0.0141(8) Uani 1 1 d .
C13 C 0.7102(4) 0.6793(3) 1.1295(4) 0.0153(8) Uani 1 1 d .
C14 C 0.6822(4) 0.5905(3) 1.1894(4) 0.0186(9) Uani 1 1 d .
C15 C 0.7128(5) 0.5118(3) 1.1004(5) 0.0299(11) Uani 1 1 d .
H15A H 0.8097 0.5059 1.0912 0.045 Uiso 1 1 calc R
H15B H 0.6715 0.5187 1.0077 0.045 Uiso 1 1 calc R
H15C H 0.6770 0.4602 1.1451 0.045 Uiso 1 1 calc R
C21 C 0.7096(4) 0.9904(3) 1.2021(5) 0.0223(10) Uani 1 1 d .
H21A H 0.6608 1.0454 1.2109 0.027 Uiso 1 1 calc R
H21B H 0.7690 0.9838 1.2850 0.027 Uiso 1 1 calc R
C22 C 0.6091(4) 0.9148(3) 1.1950(5) 0.0236(10) Uani 1 1 d .
H22A H 0.5706 0.9049 1.2882 0.028 Uiso 1 1 calc R
H22B H 0.5353 0.9286 1.1287 0.028 Uiso 1 1 calc R
N1 N 0.8542(3) 0.7467(2) 0.9713(4) 0.0140(7) Uani 1 1 d .
N2 N 0.8021(3) 0.6756(2) 1.0266(3) 0.0145(7) Uani 1 1 d .
N5 N 1.2587(3) 0.7363(2) 0.5589(4) 0.0178(8) Uani 1 1 d .
N21 N 0.7918(4) 0.9914(2) 1.0712(4) 0.0191(8) Uani 1 1 d .
H21C H 0.8717 1.0189 1.0878 0.023 Uiso 1 1 calc R
H21D H 0.7468 1.0199 1.0008 0.023 Uiso 1 1 calc R
N22 N 0.6817(3) 0.8356(2) 1.1475(3) 0.0151(7) Uani 1 1 d .
O4 O 0.6391(3) 0.57968(18) 1.3094(3) 0.0233(7) Uani 1 1 d .
O5 O 1.3095(3) 0.6655(2) 0.5237(3) 0.0252(7) Uani 1 1 d .
O6 O 1.2983(3) 0.8076(2) 0.5130(3) 0.0279(7) Uani 1 1 d .
O11 O 0.9624(3) 0.89229(17) 0.8764(3) 0.0175(6) Uani 1 1 d .
Cu1 Cu 0.82396(5) 0.86707(3) 1.01619(5) 0.01494(16) 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
O11 C1 C6 122.6(4)
O11 C1 C2 119.0(3)
C6 C1 C2 118.5(3)
N1 C2 C3 126.8(3)
N1 C2 C1 112.8(3)
C3 C2 C1 120.4(3)
C4 C3 C2 120.6(4)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 118.4(4)
C3 C4 H4 120.8
C5 C4 H4 120.8
C4 C5 C6 122.9(4)
C4 C5 N5 119.6(3)
C6 C5 N5 117.5(3)
C1 C6 C5 119.2(4)
C1 C6 H6 120.4
C5 C6 H6 120.4
C12 C11 H11A 109.5
C12 C11 H11B 109.5
H11A C11 H11B 109.5
C12 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N22 C12 C13 120.4(4)
N22 C12 C11 120.6(3)
C13 C12 C11 118.9(3)
N2 C13 C12 127.6(4)
N2 C13 C14 111.5(3)
C12 C13 C14 120.9(3)
O4 C14 C13 122.6(4)
O4 C14 C15 118.9(4)
C13 C14 C15 118.5(3)
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
N21 C21 C22 109.6(3)
N21 C21 H21A 109.8
C22 C21 H21A 109.8
N21 C21 H21B 109.8
C22 C21 H21B 109.8
H21A C21 H21B 108.2
N22 C22 C21 108.5(3)
N22 C22 H22A 110.0
C21 C22 H22A 110.0
N22 C22 H22B 110.0
C21 C22 H22B 110.0
H22A C22 H22B 108.4
N2 N1 C2 117.4(3)
N2 N1 Cu1 130.2(3)
C2 N1 Cu1 112.3(2)
N1 N2 C13 121.7(3)
O6 N5 O5 123.0(3)
O6 N5 C5 118.8(3)
O5 N5 C5 118.2(3)
C21 N21 Cu1 107.2(2)
C21 N21 H21C 110.3
Cu1 N21 H21C 110.3
C21 N21 H21D 110.3
Cu1 N21 H21D 110.3
H21C N21 H21D 108.5
C12 N22 C22 121.3(3)
C12 N22 Cu1 128.2(3)
C22 N22 Cu1 110.3(3)
C1 O11 Cu1 110.1(2)
N1 Cu1 N22 91.07(14)
N1 Cu1 O11 85.87(13)
N22 Cu1 O11 176.18(12)
N1 Cu1 N21 177.70(14)
N22 Cu1 N21 87.23(14)
O11 Cu1 N21 95.89(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O11 1.332(5)
C1 C6 1.383(5)
C1 C2 1.435(5)
C2 N1 1.392(5)
C2 C3 1.394(5)
C3 C4 1.379(6)
C3 H3 0.9300
C4 C5 1.384(5)
C4 H4 0.9300
C5 C6 1.398(5)
C5 N5 1.460(5)
C6 H6 0.9300
C11 C12 1.504(5)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 N22 1.307(5)
C12 C13 1.461(5)
C13 N2 1.334(5)
C13 C14 1.491(6)
C14 O4 1.220(5)
C14 C15 1.495(6)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C21 N21 1.481(5)
C21 C22 1.517(6)
C21 H21A 0.9700
C21 H21B 0.9700
C22 N22 1.475(5)
C22 H22A 0.9700
C22 H22B 0.9700
N1 N2 1.308(4)
N1 Cu1 1.906(3)
N5 O6 1.233(4)
N5 O5 1.237(4)
N21 Cu1 1.989(3)
N21 H21C 0.9000
N21 H21D 0.9000
N22 Cu1 1.938(3)
O11 Cu1 1.942(3)
