#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:43:56 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180051 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/45/7034538.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_7034538
loop_
_publ_author_name
'Wu, Li'
'Zhong, Wei'
'Xu, Beibei'
'Wei, Zhenhong'
'Liu, Xiaoming'
_publ_section_title
;
 Synthesis and characterization of copper(ii) complexes with multidentate
 ligands as catalysts for the direct hydroxylation of benzene to phenol.
;
_journal_issue                   17
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8013
_journal_page_last               8020
_journal_paper_doi               10.1039/c5dt00575b
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C36 H38 Cu2 N8 O2, 2(Cl O4)'
_chemical_formula_sum            'C36 H38 Cl2 Cu2 N8 O10'
_chemical_formula_weight         940.74
_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
_audit_update_record
;
2015-03-02 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 116.68(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.006(5)
_cell_length_b                   9.927(4)
_cell_length_c                   17.447(6)
_cell_measurement_reflns_used    4091
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.778
_cell_measurement_theta_min      2.432
_cell_volume                     1858.0(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0785
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12925
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    1.360
_exptl_absorpt_correction_T_max  0.794
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SHELXTL'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.865
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.1071
_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)+(0.0636P)²+27.2568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2503
_refine_ls_wR_factor_ref         0.2563
_reflns_number_gt                2837
_reflns_number_total             3265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5dt00575b2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7034537--7034538.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7034538
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
Cu1 Cu 0.39030(10) 0.46615(12) 1.02176(7) 0.0285(4) Uani 1 1 d .
N1 N 0.2036(7) 0.5118(9) 0.9563(5) 0.038(2) Uani 1 1 d .
N3 N 0.3325(10) 0.2838(9) 0.9811(6) 0.045(2) Uani 1 1 d .
N4 N 0.1967(14) 0.125(2) 0.9264(9) 0.109(6) Uani 1 1 d D
Cl1 Cl 0.1660(2) 0.2605(3) 0.66289(18) 0.0438(7) Uani 1 1 d .
O1 O 0.4315(6) 0.5569(7) 0.9215(4) 0.0389(17) Uani 1 1 d .
O2 O 0.0787(10) 0.3383(12) 0.5932(9) 0.113(5) Uani 1 1 d .
O3 O 0.1745(14) 0.284(2) 0.7402(9) 0.161(8) Uani 1 1 d .
O4 O 0.2765(8) 0.2544(13) 0.6571(6) 0.081(3) Uani 1 1 d .
O5 O 0.1100(11) 0.1288(11) 0.6414(8) 0.094(4) Uani 1 1 d .
N2 N 0.3938(6) 0.6329(5) 1.0843(4) 0.038(2) Uani 1 1 d GU
C1 C 0.4959(5) 0.7013(7) 1.1457(4) 0.041(2) Uani 1 1 d GU
H1 H 0.5747 0.6625 1.1680 0.049 Uiso 1 1 calc R
C2 C 0.4801(8) 0.8278(7) 1.1737(5) 0.063(4) Uani 1 1 d GU
H2 H 0.5484 0.8736 1.2147 0.076 Uiso 1 1 calc R
C3 C 0.3623(10) 0.8858(6) 1.1403(6) 0.112(6) Uani 1 1 d GU
H3 H 0.3518 0.9704 1.1590 0.135 Uiso 1 1 calc R
C4 C 0.2602(7) 0.8173(8) 1.0789(6) 0.103(6) Uani 1 1 d GU
H4 H 0.1814 0.8562 1.0565 0.124 Uiso 1 1 calc R
C5 C 0.2759(5) 0.6909(8) 1.0509(5) 0.053(3) Uani 1 1 d GU
C6 C 0.1741(10) 0.6263(17) 0.9961(8) 0.066(4) Uani 1 1 d .
H6A H 0.1211 0.6884 0.9518 0.079 Uiso 1 1 calc R
H6B H 0.1280 0.5950 1.0263 0.079 Uiso 1 1 calc R
C7 C 0.1392(10) 0.3881(16) 0.9600(8) 0.068(5) Uani 1 1 d .
H7A H 0.0558 0.3860 0.9129 0.081 Uiso 1 1 calc R
H7B H 0.1327 0.3846 1.0134 0.081 Uiso 1 1 calc R
C8 C 0.2117(17) 0.2732(14) 0.9543(7) 0.067(4) Uani 1 1 d .
C10 C 0.3004(10) 0.0633(11) 0.9380(7) 0.043(3) Uani 1 1 d .
H10 H 0.3131 -0.0251 0.9262 0.052 Uiso 1 1 calc R
C11 C 0.3831(13) 0.1654(12) 0.9720(7) 0.053(3) Uani 1 1 d .
H11 H 0.4677 0.1556 0.9880 0.063 Uiso 1 1 calc R
C12 C 0.1709(9) 0.5396(11) 0.8648(6) 0.036(2) Uani 1 1 d .
H12A H 0.1890 0.4591 0.8408 0.043 Uiso 1 1 calc R
H12B H 0.0816 0.5543 0.8344 0.043 Uiso 1 1 calc R
C13 C 0.2335(8) 0.6551(9) 0.8460(6) 0.028(2) Uani 1 1 d .
C14 C 0.1597(9) 0.7575(10) 0.7908(6) 0.035(2) Uani 1 1 d .
H14 H 0.0749 0.7590 0.7754 0.042 Uiso 1 1 calc R
C15 C 0.2074(10) 0.8535(10) 0.7594(7) 0.040(3) Uani 1 1 d .
H15 H 0.1566 0.9207 0.7235 0.048 Uiso 1 1 calc R
C16 C 0.3344(11) 0.8502(11) 0.7818(7) 0.047(3) Uani 1 1 d .
H16 H 0.3692 0.9148 0.7605 0.056 Uiso 1 1 calc R
C17 C 0.4077(9) 0.7508(12) 0.8356(6) 0.041(3) Uani 1 1 d .
H17 H 0.4922 0.7500 0.8497 0.049 Uiso 1 1 calc R
C18 C 0.3628(9) 0.6539(11) 0.8691(6) 0.035(2) Uani 1 1 d .
C9 C 0.071(2) 0.075(4) 0.8937(13) 0.182(16) Uani 1 1 d D
H9A H 0.0387 0.0586 0.8333 0.273 Uiso 1 1 calc R
H9B H 0.0203 0.1411 0.9034 0.273 Uiso 1 1 calc R
H9C H 0.0710 -0.0069 0.9226 0.273 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 '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
O1 Cu1 N3 102.0(4) 3_667 .
O1 Cu1 N2 94.2(3) 3_667 .
N3 Cu1 N2 153.4(4) . .
O1 Cu1 N1 173.4(3) 3_667 .
N3 Cu1 N1 83.2(4) . .
N2 Cu1 N1 82.5(3) . .
O1 Cu1 O1 82.1(3) 3_667 .
N3 Cu1 O1 105.0(3) . .
N2 Cu1 O1 98.0(3) . .
N1 Cu1 O1 92.6(3) . .
C6 N1 C7 112.7(11) . .
C6 N1 C12 111.3(9) . .
C7 N1 C12 108.2(9) . .
C6 N1 Cu1 110.2(6) . .
C7 N1 Cu1 104.8(7) . .
C12 N1 Cu1 109.4(6) . .
C8 N3 C11 111.6(11) . .
C8 N3 Cu1 111.0(9) . .
C11 N3 Cu1 137.4(9) . .
C10 N4 C9 131(2) . .
C10 N4 C8 115.3(15) . .
C9 N4 C8 114(2) . .
O3 Cl1 O4 116.4(8) . .
O3 Cl1 O2 117.7(11) . .
O4 Cl1 O2 109.0(8) . .
O3 Cl1 O5 103.6(11) . .
O4 Cl1 O5 107.1(8) . .
O2 Cl1 O5 101.0(7) . .
C18 O1 Cu1 130.0(7) . 3_667
C18 O1 Cu1 123.3(6) . .
Cu1 O1 Cu1 97.9(3) 3_667 .
C1 N2 C5 120.0 . .
C1 N2 Cu1 128.9(4) . .
C5 N2 Cu1 110.5(4) . .
C2 C1 N2 120.0 . .
C2 C1 H1 120.0 . .
N2 C1 H1 120.0 . .
C1 C2 C3 120.0 . .
C1 C2 H2 120.0 . .
C3 C2 H2 120.0 . .
C2 C3 C4 120.0 . .
C2 C3 H3 120.0 . .
C4 C3 H3 120.0 . .
C5 C4 C3 120.0 . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
C6 C5 C4 117.5(8) . .
C6 C5 N2 122.4(8) . .
C4 C5 N2 120.0 . .
C5 C6 N1 112.1(9) . .
C5 C6 H6A 109.2 . .
N1 C6 H6A 109.2 . .
C5 C6 H6B 109.2 . .
N1 C6 H6B 109.2 . .
H6A C6 H6B 107.9 . .
N1 C7 C8 107.9(10) . .
N1 C7 H7A 110.1 . .
C8 C7 H7A 110.1 . .
N1 C7 H7B 110.1 . .
C8 C7 H7B 110.1 . .
H7A C7 H7B 108.4 . .
N3 C8 C7 120.6(12) . .
N3 C8 N4 98.3(14) . .
C7 C8 N4 141.2(15) . .
N4 C10 C11 100.1(13) . .
N4 C10 H10 129.9 . .
C11 C10 H10 129.9 . .
C10 C11 N3 114.7(12) . .
C10 C11 H11 122.6 . .
N3 C11 H11 122.6 . .
C13 C12 N1 117.6(8) . .
C13 C12 H12A 107.9 . .
N1 C12 H12A 107.9 . .
C13 C12 H12B 107.9 . .
N1 C12 H12B 107.9 . .
H12A C12 H12B 107.2 . .
C14 C13 C18 118.3(9) . .
C14 C13 C12 118.9(8) . .
C18 C13 C12 121.9(8) . .
C15 C14 C13 122.5(9) . .
C15 C14 H14 118.7 . .
C13 C14 H14 118.7 . .
C14 C15 C16 118.6(9) . .
C14 C15 H15 120.7 . .
C16 C15 H15 120.7 . .
C17 C16 C15 119.6(10) . .
C17 C16 H16 120.2 . .
C15 C16 H16 120.2 . .
C18 C17 C16 123.1(10) . .
C18 C17 H17 118.4 . .
C16 C17 H17 118.4 . .
O1 C18 C17 124.5(9) . .
O1 C18 C13 117.6(9) . .
C17 C18 C13 117.9(9) . .
N4 C9 H9A 109.5 . .
N4 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N4 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.926(7) 3_667
Cu1 N3 1.954(10) .
Cu1 N2 1.973(5) .
Cu1 N1 2.058(8) .
Cu1 O1 2.211(7) .
N1 C6 1.457(16) .
N1 C7 1.468(16) .
N1 C12 1.490(12) .
N3 C8 1.313(19) .
N3 C11 1.364(16) .
N4 C10 1.319(18) .
N4 C9 1.44(3) .
N4 C8 1.53(2) .
Cl1 O3 1.327(13) .
Cl1 O4 1.376(10) .
Cl1 O2 1.425(11) .
Cl1 O5 1.440(11) .
O1 C18 1.329(11) .
O1 Cu1 1.926(6) 3_667
N2 C1 1.3900 .
N2 C5 1.3900 .
C1 C2 1.3900 .
C1 H1 0.9300 .
C2 C3 1.3900 .
C2 H2 0.9300 .
C3 C4 1.3900 .
C3 H3 0.9300 .
C4 C5 1.3900 .
C4 H4 0.9300 .
C5 C6 1.330(15) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.47(2) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C10 C11 1.355(16) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 C13 1.486(14) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.406(12) .
C13 C18 1.417(13) .
C14 C15 1.349(15) .
C14 H14 0.9300 .
C15 C16 1.393(16) .
C15 H15 0.9300 .
C16 C17 1.373(15) .
C16 H16 0.9300 .
C17 C18 1.357(15) .
C17 H17 0.9300 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
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
O1 Cu1 N1 C6 -67(3) 3_667 .
N3 Cu1 N1 C6 150.9(9) . .
N2 Cu1 N1 C6 -6.6(8) . .
O1 Cu1 N1 C6 -104.3(8) . .
O1 Cu1 N1 C7 172(3) 3_667 .
N3 Cu1 N1 C7 29.4(8) . .
N2 Cu1 N1 C7 -128.1(8) . .
O1 Cu1 N1 C7 134.2(8) . .
O1 Cu1 N1 C12 56(3) 3_667 .
N3 Cu1 N1 C12 -86.5(7) . .
N2 Cu1 N1 C12 116.1(7) . .
O1 Cu1 N1 C12 18.4(7) . .
O1 Cu1 N3 C8 168.2(7) 3_667 .
N2 Cu1 N3 C8 42.0(12) . .
N1 Cu1 N3 C8 -15.9(8) . .
O1 Cu1 N3 C8 -106.8(8) . .
O1 Cu1 N3 C11 -12.9(11) 3_667 .
N2 Cu1 N3 C11 -139.0(10) . .
N1 Cu1 N3 C11 163.0(11) . .
O1 Cu1 N3 C11 72.1(11) . .
O1 Cu1 O1 C18 -150.2(9) 3_667 .
N3 Cu1 O1 C18 109.5(8) . .
N2 Cu1 O1 C18 -57.0(8) . .
N1 Cu1 O1 C18 25.8(8) . .
O1 Cu1 O1 Cu1 0.0 3_667 3_667
N3 Cu1 O1 Cu1 -100.4(4) . 3_667
N2 Cu1 O1 Cu1 93.2(3) . 3_667
N1 Cu1 O1 Cu1 175.9(4) . 3_667
O1 Cu1 N2 C1 0.9(5) 3_667 .
N3 Cu1 N2 C1 128.5(7) . .
N1 Cu1 N2 C1 -173.4(5) . .
O1 Cu1 N2 C1 -81.8(5) . .
O1 Cu1 N2 C5 172.5(4) 3_667 .
N3 Cu1 N2 C5 -59.9(8) . .
N1 Cu1 N2 C5 -1.8(4) . .
O1 Cu1 N2 C5 89.9(4) . .
C5 N2 C1 C2 0.0 . .
Cu1 N2 C1 C2 171.0(6) . .
N2 C1 C2 C3 0.0 . .
C1 C2 C3 C4 0.0 . .
C2 C3 C4 C5 0.0 . .
C3 C4 C5 C6 175.9(10) . .
C3 C4 C5 N2 0.0 . .
C1 N2 C5 C6 -175.7(10) . .
Cu1 N2 C5 C6 11.8(10) . .
C1 N2 C5 C4 0.0 . .
Cu1 N2 C5 C4 -172.5(5) . .
C4 C5 C6 N1 166.5(8) . .
N2 C5 C6 N1 -17.8(15) . .
C7 N1 C6 C5 130.8(11) . .
C12 N1 C6 C5 -107.5(11) . .
Cu1 N1 C6 C5 14.1(13) . .
C6 N1 C7 C8 -155.8(9) . .
C12 N1 C7 C8 80.7(10) . .
Cu1 N1 C7 C8 -36.0(11) . .
C11 N3 C8 C7 178.6(10) . .
Cu1 N3 C8 C7 -2.1(14) . .
C11 N3 C8 N4 -0.2(12) . .
Cu1 N3 C8 N4 179.1(7) . .
N1 C7 C8 N3 27.5(15) . .
N1 C7 C8 N4 -154.4(14) . .
C10 N4 C8 N3 0.3(14) . .
C9 N4 C8 N3 178.8(12) . .
C10 N4 C8 C7 -178.0(15) . .
C9 N4 C8 C7 0(2) . .
C9 N4 C10 C11 -178.5(16) . .
C8 N4 C10 C11 -0.3(14) . .
N4 C10 C11 N3 0.2(13) . .
C8 N3 C11 C10 0.0(14) . .
Cu1 N3 C11 C10 -179.0(8) . .
C6 N1 C12 C13 60.2(12) . .
C7 N1 C12 C13 -175.5(10) . .
Cu1 N1 C12 C13 -61.8(10) . .
N1 C12 C13 C14 -123.3(10) . .
N1 C12 C13 C18 68.2(13) . .
C18 C13 C14 C15 0.0(15) . .
C12 C13 C14 C15 -168.9(10) . .
C13 C14 C15 C16 0.7(16) . .
C14 C15 C16 C17 -0.6(16) . .
C15 C16 C17 C18 -0.2(18) . .
Cu1 O1 C18 C17 9.3(16) 3_667 .
Cu1 O1 C18 C17 149.2(9) . .
Cu1 O1 C18 C13 -171.4(7) 3_667 .
Cu1 O1 C18 C13 -31.5(12) . .
C16 C17 C18 O1 -179.7(10) . .
C16 C17 C18 C13 1.0(17) . .
C14 C13 C18 O1 179.7(9) . .
C12 C13 C18 O1 -11.7(14) . .
C14 C13 C18 C17 -0.9(14) . .
C12 C13 C18 C17 167.7(10) . .
