#------------------------------------------------------------------------------
#$Date: 2026-04-05 14:01:14 +0200 (Sun 05 de Apr de 2026) $
#$Revision: 305355 $
#$URL: svn://www.crystallography.net/cod/cif/7/72/01/7720112.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_7720112
loop_
_publ_author_name
'Nunes, Inês M'
'Vieira, Bruno J. C.'
'Waerenborgh, João C'
'Romeu, Maria J.'
'Teixeira-Santos, Rita'
'Carapeto, Ana P.'
'Losada-García, Noelia'
'Mergulhão, Filipe J'
'Silva, Elisabete R.'
'Alves, Luis G.'
_publ_section_title
;
 Cyclam-based Cu(II) and Fe(III) complexes for antifouling coating
 development.
;
_journal_issue                   10
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4108
_journal_page_last               4118
_journal_paper_doi               10.1039/d5dt01700a
_journal_volume                  55
_journal_year                    2026
_chemical_formula_moiety         'C34 H46 F6 N4 O4'
_chemical_formula_sum            'C34 H46 F6 N4 O4'
_chemical_formula_weight         688.75
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2025-03-13 deposited with the CCDC.	2026-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                95.539(8)
_cell_angle_beta                 91.382(8)
_cell_angle_gamma                105.270(7)
_cell_formula_units_Z            1
_cell_length_a                   5.3622(7)
_cell_length_b                   8.688(1)
_cell_length_c                   19.054(2)
_cell_measurement_reflns_used    837
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.51
_cell_measurement_theta_min      3.08
_cell_volume                     851.19(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.1024
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5551
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.755
_diffrn_reflns_theta_min         1.075
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1745
_refine_ls_R_factor_gt           0.0993
_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)+(0.1783P)²+0.0607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2686
_refine_ls_wR_factor_ref         0.3110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1597
_reflns_number_total             3269
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt01700a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7720112--7720113.cif.'
_cod_database_code               7720112
_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   0.979
_shelx_estimated_absorpt_t_max   0.993
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
N1 N 0.0745(7) 0.3119(4) 0.3858(2) 0.0286(10) Uani 1 1 d . . . . .
N2 N -0.1505(7) 0.3285(4) 0.6012(2) 0.0251(10) Uani 1 1 d . . . . .
O2 O -0.2310(7) 0.2784(5) 0.7873(2) 0.0462(11) Uani 1 1 d . . . . .
O1 O -0.5123(7) 0.1599(4) 0.6974(2) 0.0478(11) Uani 1 1 d . . . . .
C15 C -0.3026(10) 0.2446(6) 0.7192(3) 0.0310(12) Uani 1 1 d . . . . .
C8 C -0.1872(10) 0.2626(6) 0.2439(3) 0.0349(13) Uani 1 1 d . . . . .
H8 H -0.2787 0.3053 0.2796 0.042 Uiso 1 1 calc R U . . .
C7 C -0.0067(9) 0.1828(5) 0.2623(3) 0.0305(12) Uani 1 1 d . . . . .
C3 C -0.1946(9) 0.1716(5) 0.5600(3) 0.0312(12) Uani 1 1 d . . . . .
H3A H -0.3662 0.1038 0.5705 0.037 Uiso 1 1 calc R U . . .
H3B H -0.0626 0.1195 0.5757 0.037 Uiso 1 1 calc R U . . .
C4 C -0.1847(9) 0.1771(5) 0.4807(3) 0.0298(12) Uani 1 1 d . . . . .
H4A H -0.3256 0.2210 0.4640 0.036 Uiso 1 1 calc R U . . .
H4B H -0.2148 0.0665 0.4573 0.036 Uiso 1 1 calc R U . . .
C5 C 0.0727(9) 0.2791(5) 0.4592(3) 0.0277(11) Uani 1 1 d . . . . .
H5A H 0.1184 0.3825 0.4897 0.033 Uiso 1 1 calc R U . . .
H5B H 0.2082 0.2238 0.4680 0.033 Uiso 1 1 calc R U . . .
C10 C -0.1046(11) 0.2183(6) 0.1222(3) 0.0402(14) Uani 1 1 d . . . . .
C6 C 0.0444(10) 0.1641(5) 0.3387(3) 0.0336(13) Uani 1 1 d . . . . .
H6A H -0.1008 0.0797 0.3540 0.040 Uiso 1 1 calc R U . . .
H6B H 0.2037 0.1278 0.3432 0.040 Uiso 1 1 calc R U . . .
C9 C -0.2342(11) 0.2804(6) 0.1744(3) 0.0422(14) Uani 1 1 d . . . . .
H9 H -0.3571 0.3359 0.1623 0.051 Uiso 1 1 calc R U . . .
C14 C -0.0888(9) 0.3250(6) 0.6747(3) 0.0320(12) Uani 1 1 d . . . . .
H14A H -0.0182 0.4372 0.6960 0.038 Uiso 1 1 calc R U . . .
H14B H 0.0515 0.2710 0.6780 0.038 Uiso 1 1 calc R U . . .
C11 C 0.0723(11) 0.1368(7) 0.1405(3) 0.0448(15) Uani 1 1 d . . . . .
H11 H 0.1608 0.0917 0.1048 0.054 Uiso 1 1 calc R U . . .
C12 C 0.1204(10) 0.1211(6) 0.2099(3) 0.0381(13) Uani 1 1 d . . . . .
H12 H 0.2444 0.0662 0.2219 0.046 Uiso 1 1 calc R U . . .
C16 C -0.4186(13) 0.2117(8) 0.8374(3) 0.0559(18) Uani 1 1 d . . . . .
H16A H -0.3287 0.1851 0.8787 0.067 Uiso 1 1 calc R U . . .
H16B H -0.5407 0.1118 0.8151 0.067 Uiso 1 1 calc R U . . .
C13 C -0.1533(16) 0.2395(9) 0.0490(4) 0.0647(19) Uani 1 1 d . . . . .
C17 C -0.5630(13) 0.3298(8) 0.8609(4) 0.067(2) Uani 1 1 d . . . . .
H17A H -0.4402 0.4325 0.8781 0.100 Uiso 1 1 calc R U . . .
H17B H -0.6740 0.2902 0.8989 0.100 Uiso 1 1 calc R U . . .
H17C H -0.6701 0.3449 0.8210 0.100 Uiso 1 1 calc R U . . .
F1 F -0.3307(15) 0.2970(11) 0.0338(2) 0.186(4) Uani 1 1 d . . . . .
F2 F 0.0344(14) 0.3268(14) 0.0207(4) 0.226(5) Uani 1 1 d . . . . .
F3 F -0.187(3) 0.1151(10) 0.0060(3) 0.251(6) Uani 1 1 d . . . . .
C1 C 0.3173(9) 0.4279(5) 0.3714(3) 0.0300(12) Uani 1 1 d . . . . .
H1A H 0.3193 0.4379 0.3201 0.036 Uiso 1 1 calc R U . . .
H1B H 0.4640 0.3848 0.3841 0.036 Uiso 1 1 calc R U . . .
C2 C 0.3594(9) 0.5945(5) 0.4109(3) 0.0296(12) Uani 1 1 d . . . . .
H2A H 0.3787 0.5863 0.4622 0.036 Uiso 1 1 calc R U . . .
H2B H 0.5237 0.6645 0.3967 0.036 Uiso 1 1 calc 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'
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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C5 N1 C6 110.6(3) . . ?
C5 N1 C1 111.1(4) . . ?
C6 N1 C1 108.9(4) . . ?
C14 N2 C3 113.0(4) . . ?
C14 N2 C2 113.2(4) . 2_566 ?
C3 N2 C2 112.6(4) . 2_566 ?
C15 O2 C16 117.4(5) . . ?
O1 C15 O2 123.4(5) . . ?
O1 C15 C14 125.9(5) . . ?
O2 C15 C14 110.7(4) . . ?
C9 C8 C7 120.3(5) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C12 C7 C8 118.7(5) . . ?
C12 C7 C6 121.3(5) . . ?
C8 C7 C6 120.0(4) . . ?
N2 C3 C4 114.6(3) . . ?
N2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
N2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C5 112.6(4) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 C4 114.3(4) . . ?
N1 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
N1 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C9 C10 C11 119.1(5) . . ?
C9 C10 C13 120.0(6) . . ?
C11 C10 C13 120.8(6) . . ?
N1 C6 C7 113.4(4) . . ?
N1 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C9 C10 120.5(5) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
N2 C14 C15 117.9(4) . . ?
N2 C14 H14A 107.8 . . ?
C15 C14 H14A 107.8 . . ?
N2 C14 H14B 107.8 . . ?
C15 C14 H14B 107.8 . . ?
H14A C14 H14B 107.2 . . ?
C12 C11 C10 120.1(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 121.3(5) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
O2 C16 C17 109.6(5) . . ?
O2 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
O2 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
F1 C13 F2 102.1(8) . . ?
F1 C13 F3 104.5(8) . . ?
F2 C13 F3 97.8(8) . . ?
F1 C13 C10 119.1(7) . . ?
F2 C13 C10 115.1(7) . . ?
F3 C13 C10 115.3(6) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C1 C2 114.6(4) . . ?
N1 C1 H1A 108.6 . . ?
C2 C1 H1A 108.6 . . ?
N1 C1 H1B 108.6 . . ?
C2 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
N2 C2 C1 114.6(4) 2_566 . ?
N2 C2 H2A 108.6 2_566 . ?
C1 C2 H2A 108.6 . . ?
N2 C2 H2B 108.6 2_566 . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
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
N1 C5 1.455(6) . ?
N1 C6 1.462(6) . ?
N1 C1 1.471(6) . ?
N2 C14 1.438(6) . ?
N2 C3 1.464(6) . ?
N2 C2 1.472(6) 2_566 ?
O2 C15 1.328(6) . ?
O2 C16 1.451(7) . ?
O1 C15 1.209(6) . ?
C15 C14 1.503(7) . ?
C8 C9 1.373(7) . ?
C8 C7 1.387(7) . ?
C8 H8 0.9500 . ?
C7 C12 1.369(7) . ?
C7 C6 1.507(7) . ?
C3 C4 1.519(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.520(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C10 C9 1.375(8) . ?
C10 C11 1.381(8) . ?
C10 C13 1.451(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C9 H9 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C11 C12 1.367(8) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C16 C17 1.483(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C13 F1 1.226(8) . ?
C13 F2 1.258(9) . ?
C13 F3 1.262(9) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C1 C2 1.525(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.472(6) 2_566 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
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
C3 H3A O1 0.99 2.60 3.153(6) 115.3 .
C6 H6A O1 0.99 2.61 3.441(6) 141.1 2_456
C2 H2B O1 0.99 2.47 3.082(6) 119.3 2_566
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 O2 C15 O1 -1.3(7) . . . . ?
C16 O2 C15 C14 179.0(4) . . . . ?
C9 C8 C7 C12 -0.7(7) . . . . ?
C9 C8 C7 C6 179.9(4) . . . . ?
C14 N2 C3 C4 -163.5(4) . . . . ?
C2 N2 C3 C4 66.7(5) 2_566 . . . ?
N2 C3 C4 C5 58.3(5) . . . . ?
C6 N1 C5 C4 -66.5(5) . . . . ?
C1 N1 C5 C4 172.6(4) . . . . ?
C3 C4 C5 N1 -169.3(4) . . . . ?
C5 N1 C6 C7 168.9(4) . . . . ?
C1 N1 C6 C7 -68.8(5) . . . . ?
C12 C7 C6 N1 135.0(5) . . . . ?
C8 C7 C6 N1 -45.6(6) . . . . ?
C7 C8 C9 C10 0.5(7) . . . . ?
C11 C10 C9 C8 0.4(8) . . . . ?
C13 C10 C9 C8 -179.2(5) . . . . ?
C3 N2 C14 C15 -72.2(5) . . . . ?
C2 N2 C14 C15 57.3(5) 2_566 . . . ?
O1 C15 C14 N2 12.7(7) . . . . ?
O2 C15 C14 N2 -167.6(4) . . . . ?
C9 C10 C11 C12 -1.1(8) . . . . ?
C13 C10 C11 C12 178.5(5) . . . . ?
C10 C11 C12 C7 0.9(8) . . . . ?
C8 C7 C12 C11 0.0(7) . . . . ?
C6 C7 C12 C11 179.4(5) . . . . ?
C15 O2 C16 C17 -93.9(6) . . . . ?
C9 C10 C13 F1 -8.1(10) . . . . ?
C11 C10 C13 F1 172.2(7) . . . . ?
C9 C10 C13 F2 113.6(9) . . . . ?
C11 C10 C13 F2 -66.1(10) . . . . ?
C9 C10 C13 F3 -133.6(10) . . . . ?
C11 C10 C13 F3 46.8(12) . . . . ?
C5 N1 C1 C2 -64.5(5) . . . . ?
C6 N1 C1 C2 173.5(4) . . . . ?
N1 C1 C2 N2 -56.5(5) . . . 2_566 ?
