#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/51/7055177.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_7055177
loop_
_publ_author_name
'Silva, Telma F. S.'
'Rocha, Bruno G. M.'
'Guedes da Silva, M. Fátima C.'
'Martins, Luísa M. D. R. S.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 V(iv), Fe(ii), Ni(ii) and Cu(ii) complexes bearing
 2,2,2-tris(pyrazol-1-yl)ethyl methanesulfonate: application as catalysts
 for the cyclooctane oxidation
;
_journal_issue                   1
_journal_name_full               'New J. Chem.'
_journal_page_first              528
_journal_paper_doi               10.1039/C5NJ01865J
_journal_volume                  40
_journal_year                    2016
_chemical_formula_moiety         'C24 H28 Cu N12 O6 S2, 2(C F3 O3 S)'
_chemical_formula_sum            'C26 H28 Cu F6 N12 O12 S4'
_chemical_formula_weight         1006.38
_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
;
2015-10-24 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                101.763(3)
_cell_angle_beta                 103.543(2)
_cell_angle_gamma                100.003(3)
_cell_formula_units_Z            1
_cell_length_a                   8.2321(7)
_cell_length_b                   9.8695(8)
_cell_length_c                   12.5776(10)
_cell_measurement_reflns_used    3011
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.42
_cell_measurement_theta_min      2.62
_cell_volume                     945.92(14)
_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, 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10880
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        26.300
_diffrn_reflns_theta_max         30.555
_diffrn_reflns_theta_min         2.701
_exptl_absorpt_coefficient_mu    0.905
_exptl_absorpt_correction_T_max  0.8789
_exptl_absorpt_correction_T_min  0.7672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_description       prism
_exptl_crystal_F_000             511
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.180
_refine_diff_density_max         1.626
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         5584
_refine_ls_number_restraints     189
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0679
_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)+(0.1452P)²+1.1242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1943
_refine_ls_wR_factor_ref         0.2237
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3812
_reflns_number_total             5584
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5nj01865j2.cif
_cod_data_source_block           Compound4
_cod_depositor_comments          'Adding full bibliography for 7055177.cif.'
_cod_database_code               7055177
_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   0.725
_shelx_estimated_absorpt_t_max   0.854
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6318(4) 0.7653(3) 0.8534(3) 0.0254(6) Uani 1 1 d . . . . .
C2 C 0.6782(5) 0.6414(4) 0.7794(3) 0.0312(7) Uani 1 1 d . . . . .
H2A H 0.6106 0.5493 0.7818 0.037 Uiso 1 1 calc R U . . .
H2B H 0.6518 0.6479 0.6999 0.037 Uiso 1 1 calc R U . . .
C3 C 0.8793(7) 0.4413(5) 0.6605(4) 0.0497(11) Uani 1 1 d . . . . .
H3A H 0.9465 0.5077 0.6298 0.075 Uiso 1 1 calc R U . . .
H3B H 0.9083 0.3486 0.6437 0.075 Uiso 1 1 calc R U . . .
H3C H 0.7565 0.4306 0.6259 0.075 Uiso 1 1 calc R U . . .
C11 C 0.5721(5) 0.7712(4) 1.1233(3) 0.0333(7) Uani 1 1 d . . . . .
H11 H 0.5323 0.8077 1.1859 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6511(5) 0.6577(4) 1.1147(3) 0.0335(7) Uani 1 1 d . . . . .
H12 H 0.6757 0.6037 1.1685 0.040 Uiso 1 1 calc R U . . .
C13 C 0.6860(5) 0.6402(4) 1.0123(3) 0.0298(7) Uani 1 1 d . . . . .
H13 H 0.7402 0.5706 0.9811 0.036 Uiso 1 1 calc R U . . .
C14 C 0.2468(5) 0.8727(5) 0.7652(4) 0.0403(9) Uani 1 1 d . . . . .
H14 H 0.1715 0.9340 0.7749 0.048 Uiso 1 1 calc R U . . .
C15 C 0.2156(5) 0.7588(5) 0.6708(4) 0.0448(10) Uani 1 1 d . . . . .
H15 H 0.1191 0.7295 0.6058 0.054 Uiso 1 1 calc R U . . .
C16 C 0.3529(5) 0.6987(4) 0.6917(3) 0.0370(8) Uani 1 1 d . . . . .
H16 H 0.3710 0.6187 0.6433 0.044 Uiso 1 1 calc R U . . .
C17 C 0.8523(5) 1.1239(4) 0.9292(3) 0.0375(8) Uani 1 1 d . . . . .
H17 H 0.8807 1.2190 0.9742 0.045 Uiso 1 1 calc R U . . .
C18 C 0.9046(5) 1.0809(4) 0.8318(4) 0.0398(9) Uani 1 1 d . . . . .
H18 H 0.9723 1.1390 0.7990 0.048 Uiso 1 1 calc R U . . .
C19 C 0.8370(5) 0.9367(4) 0.7940(3) 0.0346(8) Uani 1 1 d . . . . .
H19 H 0.8475 0.8752 0.7285 0.042 Uiso 1 1 calc R U . . .
N11 N 0.5594(4) 0.8220(3) 1.0328(3) 0.0307(6) Uani 1 1 d . . . . .
N13 N 0.6295(4) 0.7396(3) 0.9633(2) 0.0270(6) Uani 1 1 d . . . . .
N14 N 0.3934(4) 0.8836(3) 0.8384(3) 0.0347(7) Uani 1 1 d . . . . .
N16 N 0.4587(4) 0.7739(3) 0.7942(3) 0.0298(6) Uani 1 1 d . . . . .
N17 N 0.7588(4) 1.0157(3) 0.9501(3) 0.0361(7) Uani 1 1 d . . . . .
N19 N 0.7523(4) 0.8987(3) 0.8680(2) 0.0258(5) Uani 1 1 d . . . . .
O11 O 1.1087(5) 0.5590(4) 0.8568(3) 0.0569(9) Uani 1 1 d . . . . .
O12 O 0.8289(6) 0.4104(4) 0.8488(3) 0.0672(11) Uani 1 1 d . . . . .
O13 O 0.8597(4) 0.6509(3) 0.8232(2) 0.0347(6) Uani 1 1 d . . . . .
S1 S 0.92681(16) 0.50735(11) 0.80637(9) 0.0421(3) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 1.0000 1.0000 0.02881(19) Uani 1 2 d S . P . .
F23 F 0.2479(16) 0.0057(9) 0.4668(9) 0.089(3) Uani 0.442(6) 1 d D U P A 1
F22 F 0.4685(18) 0.1078(15) 0.6184(6) 0.116(4) Uani 0.442(6) 1 d D U P A 1
F21 F 0.4507(14) 0.1201(12) 0.4524(8) 0.099(3) Uani 0.442(6) 1 d D U P A 1
C21 C 0.3651(15) 0.1242(13) 0.5286(8) 0.062(3) Uani 0.442(6) 1 d D U P A 1
S21 S 0.3285(8) 0.2931(7) 0.5364(5) 0.0456(13) Uani 0.442(6) 1 d D U P A 1
O21 O 0.312(3) 0.3597(15) 0.6418(9) 0.115(5) Uani 0.442(6) 1 d D U P A 1
O22 O 0.4606(18) 0.3888(19) 0.5149(13) 0.126(5) Uani 0.442(6) 1 d D U P A 1
O23 O 0.1857(13) 0.2826(9) 0.4460(6) 0.047(2) Uani 0.442(6) 1 d D U P A 1
F31 F 0.1368(13) 0.1263(11) 0.6194(7) 0.119(3) Uani 0.558(6) 1 d . U P A 2
F33 F 0.318(2) 0.0545(8) 0.5824(10) 0.127(4) Uani 0.558(6) 1 d . U P A 2
F32 F 0.111(2) 0.0432(12) 0.4467(8) 0.160(5) Uani 0.558(6) 1 d . U P A 2
C31 C 0.228(3) 0.1181(13) 0.5488(12) 0.098(4) Uani 0.558(6) 1 d . U P A 2
S31 S 0.2941(8) 0.2886(6) 0.5423(4) 0.0642(16) Uani 0.558(6) 1 d D U P A 2
O31 O 0.1686(16) 0.3465(19) 0.5031(19) 0.193(9) Uani 0.558(6) 1 d D U P A 2
O32 O 0.4254(9) 0.3637(7) 0.6406(6) 0.0570(19) Uani 0.558(6) 1 d D U P A 2
O33 O 0.393(2) 0.2709(13) 0.4559(9) 0.190(10) Uani 0.558(6) 1 d D U P A 2
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'
S S 0.1246 0.1234 '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'
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
N19 C1 N13 110.2(3) . .
N19 C1 N16 109.0(3) . .
N13 C1 N16 108.8(3) . .
N19 C1 C2 110.5(3) . .
N13 C1 C2 110.9(3) . .
N16 C1 C2 107.4(3) . .
O13 C2 C1 108.0(3) . .
O13 C2 H2A 110.1 . .
C1 C2 H2A 110.1 . .
O13 C2 H2B 110.1 . .
C1 C2 H2B 110.1 . .
H2A C2 H2B 108.4 . .
S1 C3 H3A 109.5 . .
S1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
S1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
N11 C11 C12 111.1(3) . .
N11 C11 H11 124.5 . .
C12 C11 H11 124.5 . .
C13 C12 C11 105.3(3) . .
C13 C12 H12 127.4 . .
C11 C12 H12 127.4 . .
N13 C13 C12 107.8(3) . .
N13 C13 H13 126.1 . .
C12 C13 H13 126.1 . .
N14 C14 C15 111.0(4) . .
N14 C14 H14 124.5 . .
C15 C14 H14 124.5 . .
C16 C15 C14 105.4(4) . .
C16 C15 H15 127.3 . .
C14 C15 H15 127.3 . .
C15 C16 N16 107.3(4) . .
C15 C16 H16 126.3 . .
N16 C16 H16 126.3 . .
N17 C17 C18 111.3(3) . .
N17 C17 H17 124.3 . .
C18 C17 H17 124.3 . .
C19 C18 C17 105.1(3) . .
C19 C18 H18 127.4 . .
C17 C18 H18 127.4 . .
N19 C19 C18 107.1(3) . .
N19 C19 H19 126.5 . .
C18 C19 H19 126.5 . .
C11 N11 N13 105.9(3) . .
C11 N11 Cu1 132.4(2) . .
N13 N11 Cu1 120.7(2) . .
C13 N13 N11 109.9(3) . .
C13 N13 C1 130.1(3) . .
N11 N13 C1 120.0(3) . .
C14 N14 N16 106.1(3) . .
C14 N14 Cu1 132.1(3) . .
N16 N14 Cu1 120.6(2) . .
C16 N16 N14 110.2(3) . .
C16 N16 C1 130.6(3) . .
N14 N16 C1 118.7(3) . .
C17 N17 N19 105.9(3) . .
C17 N17 Cu1 129.1(3) . .
N19 N17 Cu1 111.5(2) . .
C19 N19 N17 110.5(3) . .
C19 N19 C1 127.8(3) . .
N17 N19 C1 119.9(3) . .
C2 O13 S1 118.4(2) . .
O12 S1 O11 120.7(3) . .
O12 S1 O13 107.93(19) . .
O11 S1 O13 102.28(18) . .
O12 S1 C3 108.5(3) . .
O11 S1 C3 111.1(2) . .
O13 S1 C3 105.00(19) . .
N11 Cu1 N11 180.0 2_677 .
N11 Cu1 N14 93.80(13) 2_677 .
N11 Cu1 N14 86.20(13) . .
N11 Cu1 N14 86.20(13) 2_677 2_677
N11 Cu1 N14 93.80(13) . 2_677
N14 Cu1 N14 180.0 . 2_677
N11 Cu1 N17 99.52(12) 2_677 .
N11 Cu1 N17 80.48(12) . .
N14 Cu1 N17 84.19(12) . .
N14 Cu1 N17 95.81(12) 2_677 .
N11 Cu1 N17 80.48(12) 2_677 2_677
N11 Cu1 N17 99.52(12) . 2_677
N14 Cu1 N17 95.81(12) . 2_677
N14 Cu1 N17 84.19(12) 2_677 2_677
N17 Cu1 N17 180.0 . 2_677
F22 C21 F21 105.9(11) . .
F22 C21 F23 114.1(12) . .
F21 C21 F23 92.4(10) . .
F22 C21 S21 116.0(10) . .
F21 C21 S21 98.5(8) . .
F23 C21 S21 123.0(8) . .
O22 S21 O23 102.3(8) . .
O22 S21 O21 106.0(10) . .
O23 S21 O21 113.3(9) . .
O22 S21 C21 113.5(10) . .
O23 S21 C21 107.7(6) . .
O21 S21 C21 113.6(7) . .
F33 C31 F31 101.8(13) . .
F33 C31 F32 112.2(14) . .
F31 C31 F32 104.0(15) . .
F33 C31 S31 123.4(15) . .
F31 C31 S31 104.9(11) . .
F32 C31 S31 108.3(11) . .
O31 S31 O32 120.1(10) . .
O31 S31 O33 107.0(12) . .
O32 S31 O33 101.4(7) . .
O31 S31 C31 114.1(12) . .
O32 S31 C31 109.6(8) . .
O33 S31 C31 102.2(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N19 1.453(4) .
C1 N13 1.458(4) .
C1 N16 1.471(4) .
C1 C2 1.540(5) .
C2 O13 1.446(5) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 S1 1.741(5) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C11 N11 1.325(5) .
C11 C12 1.388(5) .
C11 H11 0.9500 .
C12 C13 1.369(5) .
C12 H12 0.9500 .
C13 N13 1.352(4) .
C13 H13 0.9500 .
C14 N14 1.308(5) .
C14 C15 1.397(6) .
C14 H14 0.9500 .
C15 C16 1.363(6) .
C15 H15 0.9500 .
C16 N16 1.353(5) .
C16 H16 0.9500 .
C17 N17 1.314(5) .
C17 C18 1.402(6) .
C17 H17 0.9500 .
C18 C19 1.374(5) .
C18 H18 0.9500 .
C19 N19 1.360(5) .
C19 H19 0.9500 .
N11 N13 1.367(4) .
N11 Cu1 1.999(3) .
N14 N16 1.366(4) .
N14 Cu1 2.021(3) .
N17 N19 1.367(4) .
N17 Cu1 2.347(3) .
O11 S1 1.436(4) .
O12 S1 1.411(4) .
O13 S1 1.600(3) .
Cu1 N11 1.999(3) 2_677
Cu1 N14 2.021(3) 2_677
Cu1 N17 2.347(3) 2_677
F23 C21 1.338(12) .
F22 C21 1.303(11) .
F21 C21 1.314(12) .
C21 S21 1.733(14) .
S21 O22 1.426(12) .
S21 O23 1.403(9) .
S21 O21 1.401(11) .
F31 C31 1.289(17) .
F33 C31 1.11(2) .
F32 C31 1.382(18) .
C31 S31 1.701(13) .
S31 O31 1.311(11) .
S31 O32 1.403(7) .
S31 O33 1.504(11) .
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
C2 H2A O32 0.99 2.30 3.042(7) 131.4 .
C2 H2B O23 0.99 2.64 3.453(10) 139.4 2_666
C2 H2B O33 0.99 2.24 3.202(14) 163.5 2_666
C3 H3A O31 0.98 2.54 3.231(17) 127.0 2_666
C3 H3C O22 0.98 2.42 3.397(16) 171.7 .
C11 H11 F22 0.95 2.43 3.339(9) 159.3 2_667
C12 H12 O11 0.95 2.62 3.171(5) 117.3 2_767
C12 H12 O21 0.95 2.32 3.049(11) 133.6 2_667
C12 H12 O32 0.95 2.70 3.322(9) 123.9 2_667
C13 H13 O12 0.95 2.39 3.304(5) 161.8 .
C13 H13 S1 0.95 2.99 3.779(4) 141.4 .
C15 H15 O23 0.95 2.42 3.202(10) 140.0 2_566
C15 H15 O31 0.95 2.34 3.249(14) 159.2 2_566
C16 H16 O22 0.95 2.82 3.77(2) 173.9 .
C16 H16 O32 0.95 2.63 3.419(9) 141.3 .
C19 H19 O23 0.95 2.34 3.281(8) 168.7 2_666
C19 H19 F32 0.95 2.57 3.194(10) 123.6 2_666
C19 H19 O33 0.95 2.62 3.301(12) 128.9 2_666
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139177243
