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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/08/7220806.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_7220806
loop_
_publ_author_name
'Sangtrirutnugul, Preeyanuch'
'Thongkam, Pech'
'Jindabot, Sudarat'
'Prabpai, Samran'
'Kongsaeree, Palangpon'
'Wittisuwannakul, Taveechai'
'Surawatanawong, Panida'
_publ_section_title
;
 Pyridine--Triazole Ligands for Copper--Catalyzed Aerobic Alcohol
 Oxidation
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA06933E
_journal_year                    2015
_chemical_formula_moiety         'C26 H18 Cu F6 N10 O6 S2'
_chemical_formula_sum            'C26 H18 Cu F6 N10 O6 S2'
_chemical_formula_weight         808.16
_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   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-04-12 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                111.653(2)
_cell_angle_beta                 92.753(2)
_cell_angle_gamma                102.528(2)
_cell_formula_units_Z            1
_cell_length_a                   8.6034(3)
_cell_length_b                   9.2137(4)
_cell_length_c                   11.0129(5)
_cell_measurement_reflns_used    8013
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      0.998
_cell_volume                     784.13(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 14
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  KappaCCD2000
_diffrn_measurement_method       CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0889
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8674
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.190
_diffrn_reflns_theta_min         2.010
_exptl_absorpt_coefficient_mu    0.925
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_description       block
_exptl_crystal_F_000             407
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.069(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0393
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1342
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2523
_reflns_number_total             2708
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ra06933e2.cif
_cod_data_source_block           shelxl
_cod_database_code               7220806
_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.
;
_shelxl_version_number           2013-4
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
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.0000 0.0000 0.5000 0.0365(2) Uani 1 2 d S . P
S2 S -0.27900(7) 0.03624(7) 0.26090(6) 0.0434(2) Uani 1 1 d . . .
N2 N 0.1343(2) 0.1828(2) 0.46624(18) 0.0362(4) Uani 1 1 d . . .
N3 N 0.2322(2) 0.1965(2) 0.38113(19) 0.0386(4) Uani 1 1 d . . .
N1 N -0.0634(2) 0.1882(2) 0.64086(19) 0.0368(4) Uani 1 1 d . . .
O1 O -0.2113(2) -0.0446(2) 0.33080(19) 0.0546(5) Uani 1 1 d . . .
C6 C 0.1175(2) 0.3294(2) 0.5457(2) 0.0342(5) Uani 1 1 d . . .
N4 N 0.2776(2) 0.3540(2) 0.40777(19) 0.0357(4) Uani 1 1 d . . .
C5 C 0.0147(2) 0.3351(3) 0.6465(2) 0.0353(5) Uani 1 1 d . . .
N5 N 0.4205(3) 0.5723(3) 0.3703(3) 0.0517(6) Uani 1 1 d . . .
C4 C -0.0010(3) 0.4774(3) 0.7434(2) 0.0428(6) Uani 1 1 d . . .
H4 H 0.0560 0.5794 0.7438 0.051 Uiso 1 1 d R U .
O3 O -0.4443(2) -0.0343(3) 0.2080(3) 0.0718(6) Uani 1 1 d . . .
C8 C 0.3851(2) 0.4124(3) 0.3299(2) 0.0398(5) Uani 1 1 d . . .
C7 C 0.2107(3) 0.4415(3) 0.5084(2) 0.0360(5) Uani 1 1 d . . .
H7 H 0.2149 0.5537 0.5543 0.043 Uiso 1 1 d R U .
C3 C -0.1002(3) 0.4664(3) 0.8351(3) 0.0515(6) Uani 1 1 d . . .
H3 H -0.1096 0.5628 0.9050 0.062 Uiso 1 1 d R U .
C12 C 0.5143(3) 0.6332(4) 0.2989(4) 0.0641(9) Uani 1 1 d . . .
H12 H 0.5465 0.7474 0.3209 0.077 Uiso 1 1 d R U .
O2 O -0.2292(3) 0.2078(2) 0.3218(2) 0.0739(7) Uani 1 1 d . . .
C1 C -0.1606(3) 0.1811(3) 0.7294(3) 0.0478(6) Uani 1 1 d . . .
H1 H -0.2182 0.0782 0.7271 0.057 Uiso 1 1 d R U .
C9 C 0.4377(3) 0.3090(3) 0.2270(3) 0.0523(6) Uani 1 1 d . . .
H9 H 0.4086 0.1958 0.2096 0.063 Uiso 1 1 d R U .
C2 C -0.1813(3) 0.3189(3) 0.8301(3) 0.0514(6) Uani 1 1 d . . .
H2 H -0.2543 0.3118 0.8921 0.062 Uiso 1 1 d R U .
F2 F -0.0209(2) 0.0635(4) 0.1487(2) 0.1101(9) Uani 1 1 d . . .
F1 F -0.1938(4) -0.1609(3) 0.0514(2) 0.1142(9) Uani 1 1 d . . .
F3 F -0.2337(3) 0.0470(3) 0.0309(2) 0.1046(8) Uani 1 1 d . . .
C13 C -0.1780(4) -0.0040(4) 0.1156(3) 0.0694(8) Uani 1 1 d . . .
C11 C 0.5713(3) 0.5400(5) 0.1913(4) 0.0668(8) Uani 1 1 d . . .
H11 H 0.6385 0.5914 0.1440 0.080 Uiso 1 1 d R U .
C10 C 0.5345(4) 0.3777(5) 0.1551(3) 0.0720(9) Uani 1 1 d . . .
H10 H 0.5707 0.3079 0.0795 0.086 Uiso 1 1 d R 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'
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'
S S 0.1246 0.1234 '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
N2 Cu1 N2 180.00(10) 2_556 .
N2 Cu1 N1 99.23(7) 2_556 .
N2 Cu1 N1 80.77(7) . .
N2 Cu1 N1 80.77(7) 2_556 2_556
N2 Cu1 N1 99.23(7) . 2_556
N1 Cu1 N1 180.0 . 2_556
N2 Cu1 O1 88.07(7) 2_556 .
N2 Cu1 O1 91.93(7) . .
N1 Cu1 O1 95.40(7) . .
N1 Cu1 O1 84.60(7) 2_556 .
N2 Cu1 O1 91.93(7) 2_556 2_556
N2 Cu1 O1 88.07(7) . 2_556
N1 Cu1 O1 84.60(7) . 2_556
N1 Cu1 O1 95.40(7) 2_556 2_556
O1 Cu1 O1 180.0 . 2_556
O3 S2 O2 117.02(14) . .
O3 S2 O1 114.50(12) . .
O2 S2 O1 114.37(13) . .
O3 S2 C13 103.52(16) . .
O2 S2 C13 101.62(15) . .
O1 S2 C13 103.00(14) . .
N3 N2 C6 110.74(17) . .
N3 N2 Cu1 135.44(15) . .
C6 N2 Cu1 113.75(15) . .
N2 N3 N4 105.11(18) . .
C1 N1 C5 118.3(2) . .
C1 N1 Cu1 127.67(16) . .
C5 N1 Cu1 113.85(14) . .
S2 O1 Cu1 141.99(11) . .
N2 C6 C7 107.3(2) . .
N2 C6 C5 117.55(18) . .
C7 C6 C5 135.1(2) . .
N3 N4 C7 112.64(17) . .
N3 N4 C8 119.90(19) . .
C7 N4 C8 127.5(2) . .
N1 C5 C4 122.2(2) . .
N1 C5 C6 113.87(18) . .
C4 C5 C6 123.9(2) . .
C8 N5 C12 115.3(3) . .
C3 C4 C5 118.2(2) . .
C3 C4 H4 122.1 . .
C5 C4 H4 119.7 . .
N5 C8 C9 126.5(2) . .
N5 C8 N4 112.4(2) . .
C9 C8 N4 121.1(2) . .
N4 C7 C6 104.17(19) . .
N4 C7 H7 136.3 . .
C6 C7 H7 119.5 . .
C2 C3 C4 120.3(2) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.7 . .
N5 C12 C11 123.2(3) . .
N5 C12 H12 121.2 . .
C11 C12 H12 115.7 . .
N1 C1 C2 122.6(2) . .
N1 C1 H1 119.9 . .
C2 C1 H1 117.4 . .
C8 C9 C10 116.2(3) . .
C8 C9 H9 119.3 . .
C10 C9 H9 124.6 . .
C3 C2 C1 118.3(2) . .
C3 C2 H2 120.0 . .
C1 C2 H2 121.6 . .
F3 C13 F1 106.4(3) . .
F3 C13 F2 108.5(3) . .
F1 C13 F2 106.2(3) . .
F3 C13 S2 113.1(3) . .
F1 C13 S2 111.4(3) . .
F2 C13 S2 110.8(2) . .
C10 C11 C12 119.5(3) . .
C10 C11 H11 121.4 . .
C12 C11 H11 119.1 . .
C11 C10 C9 119.3(3) . .
C11 C10 H10 122.1 . .
C9 C10 H10 118.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 1.9922(17) 2_556
Cu1 N2 1.9922(17) .
Cu1 N1 2.0535(19) .
Cu1 N1 2.0535(19) 2_556
Cu1 O1 2.3941(17) .
Cu1 O1 2.3942(17) 2_556
S2 O3 1.423(2) .
S2 O2 1.424(2) .
S2 O1 1.4336(18) .
S2 C13 1.814(3) .
N2 N3 1.312(3) .
N2 C6 1.355(3) .
N3 N4 1.332(3) .
N1 C1 1.325(3) .
N1 C5 1.351(3) .
C6 C7 1.366(3) .
C6 C5 1.445(3) .
N4 C7 1.346(3) .
N4 C8 1.442(3) .
C5 C4 1.391(3) .
N5 C8 1.330(3) .
N5 C12 1.333(4) .
C4 C3 1.371(4) .
C4 H4 0.9599 .
C8 C9 1.355(4) .
C7 H7 0.9600 .
C3 C2 1.366(4) .
C3 H3 0.9600 .
C12 C11 1.367(5) .
C12 H12 0.9600 .
C1 C2 1.397(4) .
C1 H1 0.9601 .
C9 C10 1.388(4) .
C9 H9 0.9601 .
C2 H2 0.9601 .
F2 C13 1.329(4) .
F1 C13 1.327(4) .
F3 C13 1.303(4) .
C11 C10 1.356(5) .
C11 H11 0.9601 .
C10 H10 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139200432
