#------------------------------------------------------------------------------
#$Date: 2026-04-05 14:01:02 +0200 (Sun 05 de Apr de 2026) $
#$Revision: 305352 $
#$URL: svn://www.crystallography.net/cod/cif/7/72/02/7720248.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_7720248
loop_
_publ_author_name
'D'Anna, Luisa'
'Froux, Aurane'
'Bonsignore, Riccardo'
'Roller, Alexander'
'Kowol, Christian R.'
'Monari, Antonio'
'Grandemange, Stéphanie'
'Barone, Giampaolo'
'Terenzi, Alessio'
_publ_section_title
;
 In medio stat virtus: asymmetric Salphen metal complexes with
 improved biological properties.
;
_journal_issue                   10
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4250
_journal_page_last               4258
_journal_paper_doi               10.1039/d5dt02881g
_journal_volume                  55
_journal_year                    2026
_chemical_formula_moiety         'C13 H10 Cl2 N2 O'
_chemical_formula_sum            'C13 H10 Cl2 N2 O'
_chemical_formula_weight         281.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-31
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2025.01.22 svn.rc7346086 for OlexSys, GUI svn.r7128)
;
_audit_update_record
;
2025-01-31 deposited with the CCDC.	2026-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.90(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.962(8)
_cell_length_b                   3.7880(6)
_cell_length_c                   23.455(7)
_cell_measurement_reflns_used    9496
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.96
_cell_measurement_theta_min      2.86
_cell_volume                     2370.4(11)
_computing_cell_refinement       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.186.0 (STOE, 2022)'
_computing_data_reduction
;
X-Area Integrate 2.5.3.0 (STOE, 2021)
X-Area LANA 2.7.5.0 (STOE, 2022)
;
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'EIGER2 500K'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
 2360 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14790
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.025
_diffrn_reflns_theta_min         2.851
_diffrn_source                   'Axo Mo'
_diffrn_source_current           0.830
_diffrn_source_power             0.050
_diffrn_source_voltage           60
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  0.9720
_exptl_absorpt_correction_T_min  0.5947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0580P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2075
_reflns_number_total             3402
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt02881g2.cif
_cod_data_source_block           ld07_2
_cod_depositor_comments
'Adding full bibliography for 7720247--7720248.cif.'
_cod_database_code               7720248
_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_max   0.989
_shelx_estimated_absorpt_t_min   0.964
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_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
Cl1 Cl 0.72129(2) 0.77984(15) 0.37655(3) 0.02278(16) Uani 1 1 d . . . . .
Cl2 Cl 0.52472(2) 0.82179(17) 0.33423(3) 0.02836(18) Uani 1 1 d . . . . .
O1 O 0.55765(6) 0.4707(4) 0.45596(7) 0.0240(4) Uani 1 1 d . . . . .
H1 H 0.579900 0.354200 0.497396 0.006(10) Uiso 0.51 1 d . . P A 1
N1 N 0.62156(8) 0.1906(5) 0.55307(9) 0.0195(4) Uani 1 1 d . . . . .
H1A H 0.5854(17) 0.201(11) 0.534(2) 0.010(12) Uiso 0.49 1 d . . P B 2
N2 N 0.54243(9) -0.1282(7) 0.56973(11) 0.0327(6) Uani 1 1 d D . . . .
H2AA H 0.5176(11) -0.282(8) 0.5795(16) 0.032(10) Uiso 0.72 1 d D . P . .
H2AB H 0.5326(14) 0.120(7) 0.5763(18) 0.029(11) Uiso 0.64 1 d D . P . .
H2B H 0.5404(13) -0.116(9) 0.5248(11) 0.024(10) Uiso 0.64 1 d D . P C 2
C1 C 0.67256(8) 0.6824(6) 0.39999(10) 0.0167(5) Uani 1 1 d . . . . .
C2 C 0.68356(9) 0.5201(6) 0.45624(10) 0.0173(5) Uani 1 1 d . . . . .
H2 H 0.717207 0.461385 0.481654 0.021 Uiso 1 1 calc R U . . .
C3 C 0.64509(9) 0.4431(6) 0.47552(10) 0.0161(5) Uani 1 1 d . . . . .
C4 C 0.59481(9) 0.5366(6) 0.43793(10) 0.0178(5) Uani 1 1 d . . . . .
C5 C 0.58550(8) 0.7016(6) 0.38085(10) 0.0192(5) Uani 1 1 d . . . . .
C6 C 0.62375(9) 0.7709(6) 0.36171(10) 0.0177(5) Uani 1 1 d . . . . .
H6 H 0.616902 0.878369 0.322659 0.021 Uiso 1 1 calc R U . . .
C7 C 0.65667(9) 0.2666(6) 0.53445(10) 0.0187(5) Uani 1 1 d . . . . .
H7 H 0.690393 0.206974 0.559400 0.022 Uiso 1 1 calc R U . . .
C8 C 0.63064(9) 0.0366(6) 0.61116(10) 0.0163(5) Uani 1 1 d . . . . .
C9 C 0.67693(9) 0.0401(6) 0.66077(10) 0.0184(5) Uani 1 1 d . . . . .
H9 H 0.704965 0.141497 0.655391 0.022 Uiso 1 1 calc R U . . .
C10 C 0.68307(9) -0.0994(6) 0.71728(11) 0.0224(5) Uani 1 1 d . . . . .
H10 H 0.714944 -0.095448 0.750647 0.027 Uiso 1 1 calc R U . . .
C11 C 0.64212(9) -0.2457(6) 0.72479(11) 0.0214(5) Uani 1 1 d . . . . .
H11 H 0.645939 -0.342533 0.763735 0.026 Uiso 1 1 calc R U . . .
C12 C 0.59578(9) -0.2531(6) 0.67655(11) 0.0212(5) Uani 1 1 d . . . . .
H12 H 0.568081 -0.352560 0.682974 0.025 Uiso 1 1 calc R U . . .
C13 C 0.58880(9) -0.1175(6) 0.61860(11) 0.0226(5) 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C4 O1 H1 95.40(16) . . ?
C7 N1 H1A 133(2) . . ?
C7 N1 C8 123.1(2) . . ?
C8 N1 H1A 103(2) . . ?
H2AA N2 H2AB 104(3) . . ?
H2AA N2 H2B 119(3) . . ?
H2AB N2 H2B 102(3) . . ?
C13 N2 H2AA 112(2) . . ?
C13 N2 H2AB 95(2) . . ?
C13 N2 H2B 120(2) . . ?
C2 C1 Cl1 118.93(18) . . ?
C2 C1 C6 121.7(2) . . ?
C6 C1 Cl1 119.39(17) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 C7 119.3(2) . . ?
C4 C3 C7 120.4(2) . . ?
O1 C4 C3 121.2(2) . . ?
O1 C4 C5 120.6(2) . . ?
C5 C4 C3 118.1(2) . . ?
C4 C5 Cl2 119.28(18) . . ?
C6 C5 Cl2 119.61(18) . . ?
C6 C5 C4 121.1(2) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
N1 C7 C3 120.4(2) . . ?
N1 C7 H7 119.8 . . ?
C3 C7 H7 119.8 . . ?
N1 C8 C13 116.3(2) . . ?
C9 C8 N1 124.1(2) . . ?
C9 C8 C13 119.5(2) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.6(2) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.9(2) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.3(2) . . ?
C13 C12 H12 119.4 . . ?
N2 C13 C8 120.7(2) . . ?
N2 C13 C12 121.5(2) . . ?
C12 C13 C8 117.8(2) . . ?
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
Cl1 C1 1.742(2) . ?
Cl2 C5 1.733(2) . ?
O1 H1 1.0329(16) . ?
O1 C4 1.324(3) . ?
N1 H1A 0.97(4) . ?
N1 C7 1.286(3) . ?
N1 C8 1.410(3) . ?
N2 H2AA 1.02(2) . ?
N2 H2AB 1.01(2) . ?
N2 H2B 1.03(2) . ?
N2 C13 1.386(3) . ?
C1 C2 1.376(3) . ?
C1 C6 1.389(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(3) . ?
C3 C4 1.423(3) . ?
C3 C7 1.452(3) . ?
C4 C5 1.405(3) . ?
C5 C6 1.373(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.392(3) . ?
C8 C13 1.416(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.373(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(3) . ?
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
Cl1 C1 C2 C3 179.65(17) . . . . ?
Cl1 C1 C6 C5 -178.48(17) . . . . ?
Cl2 C5 C6 C1 178.31(17) . . . . ?
O1 C4 C5 Cl2 0.5(3) . . . . ?
O1 C4 C5 C6 -180.0(2) . . . . ?
N1 C8 C9 C10 176.9(2) . . . . ?
N1 C8 C13 N2 3.0(3) . . . . ?
N1 C8 C13 C12 -176.2(2) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C3 C7 179.0(2) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
C2 C3 C4 O1 -178.88(19) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C2 C3 C7 N1 -179.6(2) . . . . ?
C3 C4 C5 Cl2 -179.53(17) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C3 C7 N1 0.5(3) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C7 N1 C8 C9 18.8(3) . . . . ?
C7 N1 C8 C13 -163.5(2) . . . . ?
C7 C3 C4 O1 1.0(3) . . . . ?
C7 C3 C4 C5 -178.9(2) . . . . ?
C8 N1 C7 C3 -176.5(2) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C8 C13 N2 -179.2(2) . . . . ?
C9 C8 C13 C12 1.5(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 C12 C13 N2 179.2(2) . . . . ?
C11 C12 C13 C8 -1.6(3) . . . . ?
C13 C8 C9 C10 -0.7(3) . . . . ?
