#------------------------------------------------------------------------------
#$Date: 2020-07-06 05:10:51 +0200 (lun 06 de jul de 2020) $
#$Revision: 253906 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/44/7704449.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_7704449
loop_
_publ_author_name
'Cheng, Mei-Ling'
'Qin, Meng-Na'
'Sun, Lin'
'Liu, Lu'
'Liu, Qi'
'Tang, Xiao-Yan'
_publ_section_title
;
 Highly efficient Cu(ii)-pyrazoledicarboxylate heterogeneous catalysts for
 a base-free aerobic oxidation of benzylic alcohol to benzaldehyde with
 hydrogen peroxide as the oxidant.
;
_journal_issue                   23
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7758
_journal_page_last               7765
_journal_paper_doi               10.1039/c9dt04927d
_journal_volume                  49
_journal_year                    2020
_chemical_formula_sum            'C8 H6 Cu N4 O4'
_chemical_formula_weight         285.71
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-08-27 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.741(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2659(15)
_cell_length_b                   10.3109(14)
_cell_length_c                   8.5702(12)
_cell_measurement_reflns_used    2929
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.505
_cell_measurement_theta_min      2.677
_cell_volume                     995.4(2)
_computing_cell_refinement       'Bruker Smart (Bruker, 2005)'
_computing_data_collection       'Bruker Smart (Bruker, 2005)'
_computing_data_reduction        'Bruker Saint v7.23A (Bruker, 2005)'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6775
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.485
_diffrn_reflns_theta_min         2.678
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.204
_exptl_absorpt_correction_T_max  0.703
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0463P)²+0.0953P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0863
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2134
_reflns_number_total             2642
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt04927d2.cif
_cod_data_source_block           t
_cod_depositor_comments          'Adding full bibliography for 7704449.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7704449
_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   0.643
_shelx_estimated_absorpt_t_max   0.719
_shelxl_version_number           2013-2
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7492(2) 0.5976(2) 0.5251(3) 0.0274(5) Uani 1 1 d . . . . .
C2 C 0.6756(2) 0.5613(2) 0.6589(3) 0.0222(4) Uani 1 1 d . . . . .
C3 C 0.55686(19) 0.5892(2) 0.6917(2) 0.0198(4) Uani 1 1 d . . . . .
C4 C 0.4606(2) 0.6609(2) 0.6100(2) 0.0219(4) Uani 1 1 d . . . . .
N2 N 0.52917(16) 0.54076(18) 0.8308(2) 0.0209(4) Uani 1 1 d . . . . .
C6 C 0.8901(3) 0.4160(3) 1.1707(3) 0.0391(6) Uani 1 1 d . . . . .
H6 H 0.8830 0.4939 1.2244 0.047 Uiso 1 1 calc R U . . .
C7 C 0.9904(2) 0.3460(4) 1.1587(4) 0.0461(7) Uani 1 1 d . . . . .
H7 H 1.0645 0.3663 1.2013 0.055 Uiso 1 1 calc R U . . .
C8 C 0.8473(2) 0.2486(3) 1.0331(3) 0.0328(6) Uani 1 1 d . . . . .
H8 H 0.8061 0.1880 0.9729 0.039 Uiso 1 1 calc R U . . .
Cu1 Cu 0.62961(2) 0.39886(3) 1.09938(3) 0.02070(10) Uani 1 1 d . . . . .
N1 N 0.62642(16) 0.48174(18) 0.8923(2) 0.0224(4) Uani 1 1 d . . . . .
C5 C 0.7143(2) 0.4922(2) 0.7892(3) 0.0245(5) Uani 1 1 d . . . . .
H5 H 0.7901 0.4582 0.8028 0.029 Uiso 1 1 calc R U . . .
N3 N 0.80060(16) 0.3545(2) 1.0914(2) 0.0238(4) Uani 1 1 d . . . . .
N4 N 0.9620(2) 0.2402(2) 1.0724(3) 0.0405(6) Uani 1 1 d . . . . .
H4 H 1.0089 0.1834 1.0479 0.060(11) Uiso 1 1 d R . . . .
O1 O 0.85413(16) 0.56827(18) 0.5202(2) 0.0355(4) Uani 1 1 d . . . . .
O2 O 0.69961(18) 0.6634(2) 0.4104(2) 0.0448(5) Uani 1 1 d . . . . .
H2 H 0.6297 0.6770 0.4304 0.067 Uiso 1 1 calc R U . . .
O3 O 0.47881(15) 0.71090(17) 0.47911(18) 0.0289(4) Uani 1 1 d . . . . .
O4 O 0.36355(14) 0.66722(17) 0.68167(18) 0.0286(4) 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
O1 C1 O2 120.4(2) . . ?
O1 C1 C2 121.3(2) . . ?
O2 C1 C2 118.4(2) . . ?
C5 C2 C3 103.56(18) . . ?
C5 C2 C1 125.6(2) . . ?
C3 C2 C1 130.8(2) . . ?
N2 C3 C2 109.74(19) . . ?
N2 C3 C4 115.55(19) . . ?
C2 C3 C4 134.7(2) . . ?
O3 C4 O4 124.5(2) . . ?
O3 C4 C3 120.1(2) . . ?
O4 C4 C3 115.42(19) . . ?
C3 N2 N1 108.61(17) . . ?
C3 N2 Cu1 111.90(15) . 3_667 ?
N1 N2 Cu1 138.41(14) . 3_667 ?
C7 C6 N3 109.2(3) . . ?
C7 C6 H6 125.4 . . ?
N3 C6 H6 125.4 . . ?
C6 C7 N4 106.3(2) . . ?
C6 C7 H7 126.9 . . ?
N4 C7 H7 126.9 . . ?
N3 C8 N4 110.5(2) . . ?
N3 C8 H8 124.8 . . ?
N4 C8 H8 124.8 . . ?
N1 Cu1 N3 94.31(8) . . ?
N1 Cu1 N2 97.42(7) . 3_667 ?
N3 Cu1 N2 163.50(8) . 3_667 ?
N1 Cu1 O4 174.14(8) . 3_667 ?
N3 Cu1 O4 85.88(7) . 3_667 ?
N2 Cu1 O4 81.27(7) 3_667 3_667 ?
N1 Cu1 O3 95.46(7) . 2_646 ?
N3 Cu1 O3 107.31(7) . 2_646 ?
N2 Cu1 O3 83.12(7) 3_667 2_646 ?
O4 Cu1 O3 90.07(7) 3_667 2_646 ?
C5 N1 N2 107.90(18) . . ?
C5 N1 Cu1 128.65(16) . . ?
N2 N1 Cu1 123.45(13) . . ?
N1 C5 C2 110.2(2) . . ?
N1 C5 H5 124.9 . . ?
C2 C5 H5 124.9 . . ?
C8 N3 C6 106.1(2) . . ?
C8 N3 Cu1 126.79(18) . . ?
C6 N3 Cu1 126.03(17) . . ?
C8 N4 C7 107.9(2) . . ?
C8 N4 H4 127.5 . . ?
C7 N4 H4 124.6 . . ?
C1 O2 H2 109.5 . . ?
C4 O3 Cu1 119.87(14) . 2_656 ?
C4 O4 Cu1 114.59(14) . 3_667 ?
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
C1 O1 1.221(3) . ?
C1 O2 1.313(3) . ?
C1 C2 1.473(3) . ?
C2 C5 1.389(3) . ?
C2 C3 1.400(3) . ?
C3 N2 1.333(3) . ?
C3 C4 1.481(3) . ?
C4 O3 1.254(3) . ?
C4 O4 1.263(3) . ?
N2 N1 1.354(2) . ?
N2 Cu1 1.9934(17) 3_667 ?
C6 C7 1.345(4) . ?
C6 N3 1.365(3) . ?
C6 H6 0.9300 . ?
C7 N4 1.355(4) . ?
C7 H7 0.9300 . ?
C8 N3 1.314(3) . ?
C8 N4 1.335(3) . ?
C8 H8 0.9300 . ?
Cu1 N1 1.9696(18) . ?
Cu1 N3 1.9819(19) . ?
Cu1 N2 1.9934(17) 3_667 ?
Cu1 O4 1.9969(16) 3_667 ?
Cu1 O3 2.3831(17) 2_646 ?
N1 C5 1.340(3) . ?
C5 H5 0.9300 . ?
N4 H4 0.8176 . ?
O2 H2 0.8200 . ?
O3 Cu1 2.3831(17) 2_656 ?
O4 Cu1 1.9969(16) 3_667 ?
