#------------------------------------------------------------------------------
#$Date: 2017-01-09 06:36:43 +0200 (Mon, 09 Jan 2017) $
#$Revision: 190231 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/58/7055800.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_7055800
loop_
_publ_author_name
'Martins, Nuno M. R.'
'Mahmudov, Kamran T.'
'Guedes da Silva, M. Fátima C.'
'Martins, Luísa M. D. R. S.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Copper(ii) and iron(iii) complexes with arylhydrazone of ethyl
 2-cyanoacetate or formazan ligands as catalysts for oxidation of alcohols
;
_journal_issue                   12
_journal_name_full               'New J. Chem.'
_journal_page_first              10071
_journal_paper_doi               10.1039/C6NJ02161A
_journal_volume                  40
_journal_year                    2016
_chemical_formula_moiety         'C15 H16 Cu N4 O6'
_chemical_formula_sum            'C15 H16 Cu N4 O6'
_chemical_formula_weight         411.86
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-07-14 deposited with the CCDC.
2016-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                105.623(4)
_cell_angle_beta                 92.203(4)
_cell_angle_gamma                109.315(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3116(5)
_cell_length_b                   10.4327(8)
_cell_length_c                   10.7676(8)
_cell_measurement_reflns_used    2481
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.46
_cell_volume                     840.18(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            12529
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.544
_diffrn_reflns_theta_min         2.462
_exptl_absorpt_coefficient_mu    1.342
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_description       plate
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3021
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0494
_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)+(0.0515P)²+0.4551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2190
_reflns_number_total             3021
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6nj02161a2.cif
_cod_data_source_block           Compound2
_cod_depositor_comments
'Adding full bibliography for 7055799--7055802.cif.'
_cod_database_code               7055800
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.814
_shelx_estimated_absorpt_t_max   0.889
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.11796(6) 0.13562(5) 0.59227(5) 0.0397(2) Uani 1 1 d . .
O1 O -0.1051(3) 0.0575(3) 0.4913(3) 0.0443(8) Uani 1 1 d . .
O2 O 0.3380(3) 0.2162(3) 0.6955(3) 0.0339(7) Uani 1 1 d . .
O3 O 0.5609(3) 0.3956(3) 0.8194(3) 0.0369(7) Uani 1 1 d . .
O4 O -0.6564(3) 0.0607(3) 0.3013(3) 0.0501(8) Uani 1 1 d D .
O5 O -0.6752(4) 0.2637(4) 0.4200(3) 0.0549(9) Uani 1 1 d . .
O6 O -0.0080(4) 0.0546(4) 0.7898(4) 0.0623(10) Uani 1 1 d . .
N1 N 0.0796(4) 0.3117(3) 0.6276(3) 0.0299(7) Uani 1 1 d . .
N2 N 0.1782(4) 0.4364(3) 0.6964(3) 0.0309(8) Uani 1 1 d . .
N3 N 0.5165(5) 0.7088(4) 0.8883(4) 0.0591(12) Uani 1 1 d . .
N4 N 0.1229(5) -0.0724(4) 0.8691(4) 0.0473(10) Uani 1 1 d . .
C1 C -0.1779(4) 0.1541(4) 0.4937(4) 0.0301(9) Uani 1 1 d . .
C2 C -0.3415(5) 0.1210(4) 0.4315(4) 0.0337(10) Uani 1 1 d . .
H2 H -0.4051 0.0280 0.3823 0.040 Uiso 1 1 calc R U
C3 C -0.4102(5) 0.2269(4) 0.4426(4) 0.0308(9) Uani 1 1 d . .
C4 C -0.3149(5) 0.3669(4) 0.5128(4) 0.0349(10) Uani 1 1 d . .
H4 H -0.3621 0.4374 0.5190 0.042 Uiso 1 1 calc R U
C5 C -0.1502(5) 0.4018(4) 0.5734(4) 0.0308(9) Uani 1 1 d . .
H5 H -0.0855 0.4960 0.6189 0.037 Uiso 1 1 calc R U
C6 C -0.0818(4) 0.2964(4) 0.5663(4) 0.0278(9) Uani 1 1 d . .
C7 C -0.5922(5) 0.1887(5) 0.3871(4) 0.0377(10) Uani 1 1 d . .
C8 C 0.3322(4) 0.4515(4) 0.7542(4) 0.0310(9) Uani 1 1 d . .
C9 C 0.4347(5) 0.5962(4) 0.8281(4) 0.0395(10) Uani 1 1 d . .
C10 C 0.4064(5) 0.3454(4) 0.7525(4) 0.0313(9) Uani 1 1 d . .
C11 C 0.6441(5) 0.2935(4) 0.8213(4) 0.0384(10) Uani 1 1 d . .
H11A H 0.6500 0.2414 0.7333 0.046 Uiso 1 1 calc R U
H11B H 0.5801 0.2260 0.8644 0.046 Uiso 1 1 calc R U
C12 C 0.8222(5) 0.3771(5) 0.8946(5) 0.0495(12) Uani 1 1 d . .
H12A H 0.8818 0.3132 0.8982 0.074 Uiso 1 1 calc R U
H12B H 0.8840 0.4433 0.8510 0.074 Uiso 1 1 calc R U
H12C H 0.8144 0.4281 0.9815 0.074 Uiso 1 1 calc R U
C13 C 0.1091(5) 0.0435(5) 0.8554(5) 0.0481(12) Uani 1 1 d . .
H13 H 0.1975 0.1280 0.9002 0.058 Uiso 1 1 calc R U
C14 C -0.0044(8) -0.2109(6) 0.8060(6) 0.088(2) Uani 1 1 d . .
H14A H 0.0520 -0.2777 0.7745 0.132 Uiso 1 1 calc R U
H14B H -0.0721 -0.2062 0.7342 0.132 Uiso 1 1 calc R U
H14C H -0.0779 -0.2411 0.8672 0.132 Uiso 1 1 calc R U
C15 C 0.2701(7) -0.0690(6) 0.9470(6) 0.0735(17) Uani 1 1 d . .
H15A H 0.2320 -0.1140 1.0129 0.110 Uiso 1 1 calc R U
H15B H 0.3437 0.0281 0.9876 0.110 Uiso 1 1 calc R U
H15C H 0.3325 -0.1187 0.8925 0.110 Uiso 1 1 calc R U
H4O H -0.767(3) 0.043(7) 0.276(6) 0.110 Uiso 1 1 d D 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'
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
O2 Cu1 O1 178.71(12) . .
O2 Cu1 N1 94.56(12) . .
O1 Cu1 N1 84.40(12) . .
O2 Cu1 O1 101.99(11) . 2_556
O1 Cu1 O1 79.14(12) . 2_556
N1 Cu1 O1 161.94(13) . 2_556
O2 Cu1 Cu1 141.23(8) . 2_556
O1 Cu1 Cu1 39.89(8) . 2_556
N1 Cu1 Cu1 123.92(9) . 2_556
O1 Cu1 Cu1 39.24(7) 2_556 2_556
C1 O1 Cu1 113.3(2) . .
C1 O1 Cu1 145.2(2) . 2_556
Cu1 O1 Cu1 100.86(11) . 2_556
C10 O2 Cu1 122.6(2) . .
C10 O3 C11 116.8(3) . .
C7 O4 H4O 109(4) . .
N2 N1 C6 118.1(3) . .
N2 N1 Cu1 129.3(3) . .
C6 N1 Cu1 112.6(2) . .
N1 N2 C8 118.3(3) . .
C13 N4 C14 122.4(4) . .
C13 N4 C15 121.2(4) . .
C14 N4 C15 116.3(4) . .
O1 C1 C2 123.4(3) . .
O1 C1 C6 117.2(3) . .
C2 C1 C6 119.5(3) . .
C1 C2 C3 119.8(3) . .
C1 C2 H2 120.1 . .
C3 C2 H2 120.1 . .
C2 C3 C4 120.7(3) . .
C2 C3 C7 119.6(3) . .
C4 C3 C7 119.6(4) . .
C5 C4 C3 120.1(4) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C6 C5 C4 119.8(3) . .
C6 C5 H5 120.1 . .
C4 C5 H5 120.1 . .
C5 C6 C1 120.1(3) . .
C5 C6 N1 127.3(3) . .
C1 C6 N1 112.6(3) . .
O5 C7 O4 123.1(4) . .
O5 C7 C3 123.7(4) . .
O4 C7 C3 113.2(4) . .
N2 C8 C10 129.1(3) . .
N2 C8 C9 114.1(3) . .
C10 C8 C9 116.7(3) . .
N3 C9 C8 178.4(5) . .
O2 C10 O3 119.9(4) . .
O2 C10 C8 126.1(3) . .
O3 C10 C8 114.0(3) . .
O3 C11 C12 106.8(3) . .
O3 C11 H11A 110.4 . .
C12 C11 H11A 110.4 . .
O3 C11 H11B 110.4 . .
C12 C11 H11B 110.4 . .
H11A C11 H11B 108.6 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
O6 C13 N4 127.5(4) . .
O6 C13 H13 116.3 . .
N4 C13 H13 116.3 . .
N4 C14 H14A 109.5 . .
N4 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
N4 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N4 C15 H15A 109.5 . .
N4 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
N4 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.900(2) .
Cu1 O1 1.911(2) .
Cu1 N1 1.908(3) .
Cu1 O1 1.938(3) 2_556
Cu1 Cu1 2.9669(9) 2_556
O1 C1 1.331(4) .
O1 Cu1 1.938(3) 2_556
O2 C10 1.241(4) .
O3 C10 1.313(4) .
O3 C11 1.454(5) .
O4 C7 1.322(5) .
O4 H4O 0.89(2) .
O5 C7 1.200(5) .
O6 C13 1.235(5) .
N1 N2 1.282(4) .
N1 C6 1.412(4) .
N2 C8 1.343(5) .
N3 C9 1.136(5) .
N4 C13 1.298(6) .
N4 C14 1.439(6) .
N4 C15 1.441(6) .
C1 C2 1.383(5) .
C1 C6 1.413(5) .
C2 C3 1.382(5) .
C2 H2 0.9300 .
C3 C4 1.388(5) .
C3 C7 1.486(5) .
C4 C5 1.380(5) .
C4 H4 0.9300 .
C5 C6 1.383(5) .
C5 H5 0.9300 .
C8 C10 1.431(6) .
C8 C9 1.445(5) .
C11 C12 1.503(5) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13 0.9300 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14B O5 0.96 2.43 3.336(6) 157.8 2_456
C15 H15B N3 0.96 2.54 3.488(7) 168.4 2_667
O4 H4O O6 0.89(2) 1.81(3) 2.668(4) 161(6) 2_456
