#------------------------------------------------------------------------------
#$Date: 2017-01-09 04:17:17 +0100 (lun 09 de ene de 2017) $
#$Revision: 190117 $
#$URL: svn://www.crystallography.net/cod/cif/7/04/10/7041038.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_7041038
loop_
_publ_author_name
'Han, Li-Juan'
'Kong, Ya-Jie'
'Yan, Ting-Jiang'
'Fan, Lu-Tong'
'Zhang, Qi'
'Zhao, Hua-Jun'
'Zheng, He-Gen'
_publ_section_title
;
 A new five-coordinated copper compound for efficient degradation of
 methyl orange and Congo red in the absence of UV-visible radiation.
;
_journal_issue                   46
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              18566
_journal_page_last               18571
_journal_paper_doi               10.1039/c6dt03273g
_journal_volume                  45
_journal_year                    2016
_chemical_formula_sum            'C48 H16 Cu2 F20 N4 O8'
_chemical_formula_weight         1283.73
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-10-18 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                102.876(2)
_cell_angle_beta                 99.000(2)
_cell_angle_gamma                96.733(2)
_cell_formula_units_Z            1
_cell_length_a                   9.6512(14)
_cell_length_b                   9.9482(14)
_cell_length_c                   12.8890(18)
_cell_measurement_reflns_used    2634
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.84
_cell_measurement_theta_min      2.35
_cell_volume                     1176.6(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'BRUKER SMART 1000'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11542
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.650
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.045
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             634
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         4153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0358P)²+0.4085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0848
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3139
_reflns_number_total             4153
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt03273g2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7041038--7041040.cif.'
_cod_database_code               7041038
_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.
;
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 0.16608(3) 0.49109(4) 0.06339(3) 0.03539(13) Uani 1 1 d . .
N1 N 0.3292(2) 0.6182(2) 0.1681(2) 0.0379(6) Uani 1 1 d . .
N2 N 0.2764(2) 0.5518(2) -0.04230(19) 0.0345(6) Uani 1 1 d . .
O1 O 0.0815(2) 0.4332(2) 0.17643(17) 0.0441(5) Uani 1 1 d . .
O2 O 0.2344(3) 0.2913(3) 0.2086(3) 0.0938(10) Uani 1 1 d . .
O3 O -0.01461(18) 0.63642(19) 0.04702(16) 0.0373(5) Uani 1 1 d . .
O4 O -0.1665(2) 0.7863(2) 0.0737(2) 0.0698(8) Uani 1 1 d . .
F1 F 0.21243(18) 0.86126(19) 0.04018(15) 0.0565(5) Uani 1 1 d . .
F2 F 0.41692(19) 1.0454(2) 0.18138(19) 0.0772(7) Uani 1 1 d . .
F3 F 0.3864(3) 1.1368(2) 0.3899(2) 0.1021(9) Uani 1 1 d . .
F4 F 0.1460(3) 1.0461(2) 0.45351(17) 0.0990(8) Uani 1 1 d . .
F5 F -0.0627(2) 0.8646(2) 0.31110(18) 0.0799(7) Uani 1 1 d . .
F6 F -0.1366(2) 0.1664(2) 0.16598(16) 0.0797(7) Uani 1 1 d . .
F7 F -0.2937(2) 0.1111(3) 0.3108(2) 0.0987(8) Uani 1 1 d . .
F8 F -0.1980(3) 0.2228(3) 0.5243(2) 0.1034(9) Uani 1 1 d . .
F9 F 0.0601(3) 0.3813(3) 0.59384(18) 0.1151(10) Uani 1 1 d . .
F10 F 0.2169(2) 0.4403(3) 0.45019(19) 0.0965(8) Uani 1 1 d . .
C1 C 0.3232(3) 0.5586(3) -0.2168(3) 0.0481(8) Uani 1 1 d . .
H1A H 0.2938 0.5317 -0.2917 0.058 Uiso 1 1 calc R U
C2 C 0.4516(3) 0.6417(3) -0.1711(3) 0.0489(8) Uani 1 1 d . .
H2A H 0.5111 0.6712 -0.2146 0.059 Uiso 1 1 calc R U
C3 C 0.4914(3) 0.6809(3) -0.0601(3) 0.0451(8) Uani 1 1 d . .
H3A H 0.5778 0.7378 -0.0277 0.054 Uiso 1 1 calc R U
C4 C 0.3456(3) 0.6483(3) 0.2756(3) 0.0507(8) Uani 1 1 d . .
H4A H 0.2742 0.6111 0.3067 0.061 Uiso 1 1 calc R U
C5 C 0.4641(4) 0.7322(4) 0.3427(3) 0.0601(10) Uani 1 1 d . .
H5A H 0.4726 0.7519 0.4176 0.072 Uiso 1 1 calc R U
C6 C 0.5694(3) 0.7861(4) 0.2960(3) 0.0582(10) Uani 1 1 d . .
H6A H 0.6511 0.8419 0.3395 0.070 Uiso 1 1 calc R U
C7 C 0.5541(3) 0.7576(3) 0.1854(3) 0.0476(8) Uani 1 1 d . .
H7A H 0.6243 0.7948 0.1533 0.057 Uiso 1 1 calc R U
C8 C 0.4320(3) 0.6722(3) 0.1221(2) 0.0363(7) Uani 1 1 d . .
C9 C 0.4019(3) 0.6349(3) 0.0027(2) 0.0359(7) Uani 1 1 d . .
C10 C 0.2384(3) 0.5157(3) -0.1499(3) 0.0422(8) Uani 1 1 d . .
H10A H 0.1513 0.4594 -0.1810 0.051 Uiso 1 1 calc R U
C11 C 0.1929(3) 0.9049(3) 0.1416(2) 0.0391(7) Uani 1 1 d . .
C12 C 0.2997(3) 0.9990(3) 0.2137(3) 0.0509(9) Uani 1 1 d . .
C13 C 0.2837(4) 1.0458(4) 0.3183(3) 0.0610(10) Uani 1 1 d . .
C14 C 0.1615(4) 0.9996(4) 0.3499(3) 0.0604(10) Uani 1 1 d . .
C15 C 0.0555(4) 0.9071(3) 0.2768(3) 0.0502(8) Uani 1 1 d . .
C16 C 0.0686(3) 0.8556(3) 0.1706(2) 0.0372(7) Uani 1 1 d . .
C17 C 0.0908(4) 0.3551(4) 0.4131(3) 0.0572(9) Uani 1 1 d . .
C18 C 0.0118(5) 0.3279(4) 0.4870(3) 0.0679(11) Uani 1 1 d . .
C19 C -0.1175(4) 0.2469(4) 0.4521(3) 0.0642(11) Uani 1 1 d . .
C20 C -0.1672(3) 0.1911(4) 0.3441(3) 0.0581(10) Uani 1 1 d . .
C21 C -0.0858(3) 0.2213(3) 0.2709(3) 0.0482(8) Uani 1 1 d . .
C22 C 0.0443(3) 0.3050(3) 0.3031(3) 0.0426(8) Uani 1 1 d . .
C23 C -0.0488(3) 0.7536(3) 0.0900(3) 0.0421(8) Uani 1 1 d . .
C24 C 0.1295(3) 0.3436(4) 0.2214(3) 0.0494(8) 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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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 O3 89.84(8) . 2_565
O1 Cu1 N1 93.58(9) . .
O3 Cu1 N1 175.98(9) 2_565 .
O1 Cu1 N2 173.08(9) . .
O3 Cu1 N2 95.66(9) 2_565 .
N1 Cu1 N2 80.78(10) . .
O1 Cu1 O3 87.82(8) . .
O3 Cu1 O3 78.23(8) 2_565 .
N1 Cu1 O3 103.99(8) . .
N2 Cu1 O3 97.40(8) . .
C4 N1 C8 119.1(3) . .
C4 N1 Cu1 126.0(2) . .
C8 N1 Cu1 114.84(19) . .
C10 N2 C9 118.6(2) . .
C10 N2 Cu1 126.34(19) . .
C9 N2 Cu1 115.04(19) . .
C24 O1 Cu1 121.0(2) . .
C23 O3 Cu1 114.73(18) . 2_565
C23 O3 Cu1 142.98(19) . .
Cu1 O3 Cu1 101.77(8) 2_565 .
C2 C1 C10 118.9(3) . .
C2 C1 H1A 120.6 . .
C10 C1 H1A 120.6 . .
C1 C2 C3 119.2(3) . .
C1 C2 H2A 120.4 . .
C3 C2 H2A 120.4 . .
C2 C3 C9 119.3(3) . .
C2 C3 H3A 120.4 . .
C9 C3 H3A 120.4 . .
N1 C4 C5 122.7(3) . .
N1 C4 H4A 118.7 . .
C5 C4 H4A 118.7 . .
C6 C5 C4 118.3(3) . .
C6 C5 H5A 120.9 . .
C4 C5 H5A 120.9 . .
C7 C6 C5 120.1(3) . .
C7 C6 H6A 120.0 . .
C5 C6 H6A 120.0 . .
C6 C7 C8 118.9(3) . .
C6 C7 H7A 120.6 . .
C8 C7 H7A 120.6 . .
N1 C8 C7 121.0(3) . .
N1 C8 C9 114.8(2) . .
C7 C8 C9 124.3(3) . .
N2 C9 C3 121.5(3) . .
N2 C9 C8 114.4(2) . .
C3 C9 C8 124.1(3) . .
N2 C10 C1 122.5(3) . .
N2 C10 H10A 118.8 . .
C1 C10 H10A 118.8 . .
F1 C11 C12 117.7(3) . .
F1 C11 C16 119.8(3) . .
C12 C11 C16 122.5(3) . .
F2 C12 C13 120.3(3) . .
F2 C12 C11 120.3(3) . .
C13 C12 C11 119.3(3) . .
F3 C13 C12 120.3(4) . .
F3 C13 C14 119.9(4) . .
C12 C13 C14 119.8(3) . .
F4 C14 C15 120.2(4) . .
F4 C14 C13 119.7(4) . .
C15 C14 C13 120.2(3) . .
F5 C15 C14 118.2(3) . .
F5 C15 C16 120.0(3) . .
C14 C15 C16 121.8(3) . .
C11 C16 C15 116.4(3) . .
C11 C16 C23 121.9(3) . .
C15 C16 C23 121.6(3) . .
F10 C17 C18 118.0(3) . .
F10 C17 C22 119.3(3) . .
C18 C17 C22 122.7(3) . .
F9 C18 C19 119.7(4) . .
F9 C18 C17 120.8(4) . .
C19 C18 C17 119.4(3) . .
F8 C19 C18 119.8(4) . .
F8 C19 C20 119.8(4) . .
C18 C19 C20 120.4(3) . .
F7 C20 C19 119.9(3) . .
F7 C20 C21 121.0(4) . .
C19 C20 C21 119.1(3) . .
F6 C21 C22 119.7(3) . .
F6 C21 C20 118.2(3) . .
C22 C21 C20 122.2(3) . .
C21 C22 C17 116.2(3) . .
C21 C22 C24 121.6(3) . .
C17 C22 C24 122.1(3) . .
O4 C23 O3 125.7(3) . .
O4 C23 C16 118.9(3) . .
O3 C23 C16 115.4(3) . .
O2 C24 O1 127.4(3) . .
O2 C24 C22 119.0(3) . .
O1 C24 C22 113.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.938(2) .
Cu1 O3 1.9700(18) 2_565
Cu1 N1 2.002(2) .
Cu1 N2 2.006(2) .
Cu1 O3 2.406(2) .
N1 C4 1.329(4) .
N1 C8 1.351(3) .
N2 C10 1.332(4) .
N2 C9 1.349(3) .
O1 C24 1.260(4) .
O2 C24 1.208(4) .
O3 C23 1.278(3) .
O3 Cu1 1.9700(18) 2_565
O4 C23 1.218(3) .
F1 C11 1.333(3) .
F2 C12 1.333(4) .
F3 C13 1.336(4) .
F4 C14 1.350(4) .
F5 C15 1.343(4) .
F6 C21 1.330(4) .
F7 C20 1.328(4) .
F8 C19 1.345(4) .
F9 C18 1.346(4) .
F10 C17 1.350(4) .
C1 C2 1.372(4) .
C1 C10 1.378(4) .
C1 H1A 0.9300 .
C2 C3 1.375(4) .
C2 H2A 0.9300 .
C3 C9 1.379(4) .
C3 H3A 0.9300 .
C4 C5 1.377(4) .
C4 H4A 0.9300 .
C5 C6 1.375(5) .
C5 H5A 0.9300 .
C6 C7 1.370(4) .
C6 H6A 0.9300 .
C7 C8 1.390(4) .
C7 H7A 0.9300 .
C8 C9 1.474(4) .
C10 H10A 0.9300 .
C11 C12 1.374(4) .
C11 C16 1.380(4) .
C12 C13 1.364(5) .
C13 C14 1.369(5) .
C14 C15 1.369(5) .
C15 C16 1.381(4) .
C16 C23 1.512(4) .
C17 C18 1.363(5) .
C17 C22 1.376(5) .
C18 C19 1.355(5) .
C19 C20 1.364(5) .
C20 C21 1.378(4) .
C21 C22 1.371(4) .
C22 C24 1.520(4) .
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
C10 C1 C2 C3 -0.6(5) .
C1 C2 C3 C9 0.5(5) .
C8 N1 C4 C5 -0.3(5) .
Cu1 N1 C4 C5 177.1(3) .
N1 C4 C5 C6 -0.3(5) .
C4 C5 C6 C7 1.0(5) .
C5 C6 C7 C8 -1.0(5) .
C4 N1 C8 C7 0.3(4) .
Cu1 N1 C8 C7 -177.4(2) .
C4 N1 C8 C9 -178.7(3) .
Cu1 N1 C8 C9 3.6(3) .
C6 C7 C8 N1 0.4(5) .
C6 C7 C8 C9 179.2(3) .
C10 N2 C9 C3 -1.0(4) .
Cu1 N2 C9 C3 177.7(2) .
C10 N2 C9 C8 178.3(2) .
Cu1 N2 C9 C8 -3.0(3) .
C2 C3 C9 N2 0.3(5) .
C2 C3 C9 C8 -178.8(3) .
N1 C8 C9 N2 -0.4(4) .
C7 C8 C9 N2 -179.4(3) .
N1 C8 C9 C3 178.8(3) .
C7 C8 C9 C3 -0.1(5) .
C9 N2 C10 C1 0.9(4) .
Cu1 N2 C10 C1 -177.7(2) .
C2 C1 C10 N2 0.0(5) .
F1 C11 C12 F2 1.0(4) .
C16 C11 C12 F2 -178.9(3) .
F1 C11 C12 C13 -179.8(3) .
C16 C11 C12 C13 0.3(5) .
F2 C12 C13 F3 -1.1(5) .
C11 C12 C13 F3 179.7(3) .
F2 C12 C13 C14 178.6(3) .
C11 C12 C13 C14 -0.6(5) .
F3 C13 C14 F4 -0.3(5) .
C12 C13 C14 F4 -180.0(3) .
F3 C13 C14 C15 179.5(3) .
C12 C13 C14 C15 -0.2(5) .
F4 C14 C15 F5 -0.1(5) .
C13 C14 C15 F5 -179.9(3) .
F4 C14 C15 C16 -178.9(3) .
C13 C14 C15 C16 1.3(5) .
F1 C11 C16 C15 -179.1(3) .
C12 C11 C16 C15 0.7(5) .
F1 C11 C16 C23 -0.7(4) .
C12 C11 C16 C23 179.1(3) .
F5 C15 C16 C11 179.7(3) .
C14 C15 C16 C11 -1.5(5) .
F5 C15 C16 C23 1.3(5) .
C14 C15 C16 C23 -179.9(3) .
F10 C17 C18 F9 -1.8(6) .
C22 C17 C18 F9 -178.7(3) .
F10 C17 C18 C19 177.7(3) .
C22 C17 C18 C19 0.8(6) .
F9 C18 C19 F8 1.4(6) .
C17 C18 C19 F8 -178.1(3) .
F9 C18 C19 C20 -179.4(3) .
C17 C18 C19 C20 1.1(6) .
F8 C19 C20 F7 -1.3(5) .
C18 C19 C20 F7 179.5(3) .
F8 C19 C20 C21 177.5(3) .
C18 C19 C20 C21 -1.7(6) .
F7 C20 C21 F6 -0.9(5) .
C19 C20 C21 F6 -179.7(3) .
F7 C20 C21 C22 179.2(3) .
C19 C20 C21 C22 0.5(5) .
F6 C21 C22 C17 -178.6(3) .
C20 C21 C22 C17 1.3(5) .
F6 C21 C22 C24 3.4(5) .
C20 C21 C22 C24 -176.7(3) .
F10 C17 C22 C21 -178.8(3) .
C18 C17 C22 C21 -1.9(5) .
F10 C17 C22 C24 -0.8(5) .
C18 C17 C22 C24 176.1(3) .
Cu1 O3 C23 O4 5.4(4) 2_565
Cu1 O3 C23 O4 -164.2(2) .
Cu1 O3 C23 C16 -176.92(19) 2_565
Cu1 O3 C23 C16 13.5(5) .
C11 C16 C23 O4 -121.5(3) .
C15 C16 C23 O4 56.8(4) .
C11 C16 C23 O3 60.7(4) .
C15 C16 C23 O3 -121.0(3) .
Cu1 O1 C24 O2 5.9(5) .
Cu1 O1 C24 C22 -176.48(19) .
C21 C22 C24 O2 -107.5(4) .
C17 C22 C24 O2 74.6(5) .
C21 C22 C24 O1 74.6(4) .
C17 C22 C24 O1 -103.3(4) .
