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#$Date: 2026-04-08 00:54:40 +0200 (Wed 08 de Apr de 2026) $
#$Revision: 305472 $
#$URL: svn://www.crystallography.net/cod/cif/7/72/08/7720832.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_7720832
loop_
_publ_author_name
'Kurjan, Jakub'
'Jendželovská, Zuzana'
'Dečmanová, Viktória'
'Jendželovský, Rastislav'
'Kastratovic, Nikolina'
'Volarevic, Vladislav'
'Smolko, Lukáš'
'Smolková, Romana'
'Litecká, Miroslava'
'Zubrik, Anton'
'Jáger, Dávid'
'Varhač, Rastislav'
'Potočňák, Ivan'
_publ_section_title
;
 Structure-bioactivity relationship in copper(II) complexes with new
 halogenated coumarin derivatives.
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/d5dt02641e
_journal_year                    2026
_chemical_formula_moiety         'C17 H15 Cu N3 O7'
_chemical_formula_sum            'C17 H15 Cu N3 O7'
_chemical_formula_weight         436.86
_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   mixed
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-10-21 deposited with the CCDC.	2026-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                85.363(3)
_cell_angle_beta                 84.610(3)
_cell_angle_gamma                72.071(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2150(3)
_cell_length_b                   9.8266(5)
_cell_length_c                   10.9541(3)
_cell_measurement_reflns_used    5573
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.2840
_cell_measurement_theta_min      4.0490
_cell_volume                     836.35(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 42.74a (release 17-11-20'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9781
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.764
_diffrn_reflns_theta_min         4.060
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.309
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_description       prism
_exptl_crystal_F_000             446
_exptl_crystal_recrystallization_method 'from the synthesis'
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.999
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0468
_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)+(0.0752P)²+0.8861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1381
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2990
_reflns_number_total             3291
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt02641e2.cif
_cod_data_source_block           5
_cod_database_code               7720832
_shelx_shelxl_version_number     2019/3
_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.30589(5) 0.49858(4) 0.41538(4) 0.01879(17) Uani 1 1 d . . . . .
O4 O 0.2168(3) 0.6009(2) 0.55938(19) 0.0227(4) Uani 1 1 d . . . . .
O40 O 0.2315(3) 0.3427(2) 0.50766(19) 0.0224(4) Uani 1 1 d . . . . .
H40B H 0.154940 0.361161 0.566899 0.034 Uiso 1 1 d R U . . .
H40A H 0.265620 0.252402 0.501559 0.034 Uiso 1 1 d R U . . .
O31 O 0.0454(3) 0.5895(2) 0.33138(19) 0.0229(4) Uani 1 1 d . . . . .
O1 O 0.1275(3) 1.0204(2) 0.6294(2) 0.0234(4) Uani 1 1 d . . . . .
O2 O 0.2524(3) 1.0708(2) 0.4553(2) 0.0253(5) Uani 1 1 d . . . . .
O32 O 0.1593(3) 0.6453(3) 0.1543(2) 0.0281(5) Uani 1 1 d . . . . .
O33 O -0.1174(3) 0.6967(3) 0.1849(2) 0.0311(5) Uani 1 1 d . . . . .
N30 N 0.0297(3) 0.6444(3) 0.2213(2) 0.0215(5) Uani 1 1 d . . . . .
N13 N 0.4102(3) 0.6455(3) 0.3494(2) 0.0192(5) Uani 1 1 d . . . . .
N20 N 0.4402(3) 0.3842(3) 0.2790(2) 0.0201(5) Uani 1 1 d . . . . .
C15 C 0.5319(4) 0.4546(3) 0.2054(3) 0.0205(6) Uani 1 1 d . . . . .
C4 C 0.1949(4) 0.7332(3) 0.5739(3) 0.0216(6) Uani 1 1 d . . . . .
C11 C 0.3845(4) 0.7739(3) 0.3876(3) 0.0200(6) Uani 1 1 d . . . . .
C16 C 0.6299(4) 0.3949(3) 0.1019(3) 0.0225(6) Uani 1 1 d . . . . .
H16 H 0.693193 0.446702 0.051081 0.027 Uiso 1 1 calc R U . . .
C14 C 0.5288(4) 0.5998(3) 0.2415(3) 0.0215(6) Uani 1 1 d . . . . .
H14B H 0.645739 0.596870 0.259656 0.026 Uiso 1 1 calc R U . . .
H14A H 0.493704 0.670624 0.171920 0.026 Uiso 1 1 calc R U . . .
C2 C 0.2198(4) 0.9742(3) 0.5212(3) 0.0213(6) Uani 1 1 d . . . . .
C3 C 0.2660(4) 0.8244(3) 0.4942(3) 0.0189(6) Uani 1 1 d . . . . .
C9 C 0.0648(4) 0.9308(3) 0.7102(3) 0.0221(6) Uani 1 1 d . . . . .
C19 C 0.4441(4) 0.2517(3) 0.2512(3) 0.0210(6) Uani 1 1 d . . . . .
H19 H 0.378464 0.202372 0.302580 0.025 Uiso 1 1 calc R U . . .
C10 C 0.0902(4) 0.7896(3) 0.6842(3) 0.0205(6) Uani 1 1 d . . . . .
C17 C 0.6343(4) 0.2591(3) 0.0735(3) 0.0227(6) Uani 1 1 d . . . . .
H17 H 0.700215 0.216502 0.002746 0.027 Uiso 1 1 calc R U . . .
C5 C 0.0170(4) 0.7051(3) 0.7670(3) 0.0232(6) Uani 1 1 d . . . . .
H5 H 0.029765 0.609062 0.749602 0.028 Uiso 1 1 calc R U . . .
C18 C 0.5407(4) 0.1862(3) 0.1502(3) 0.0249(6) Uani 1 1 d . . . . .
H18 H 0.543134 0.092207 0.133306 0.030 Uiso 1 1 calc R U . . .
C12 C 0.4800(4) 0.8697(3) 0.3205(3) 0.0258(6) Uani 1 1 d . . . . .
H12C H 0.587377 0.810668 0.280457 0.039 Uiso 1 1 calc R U . . .
H12B H 0.505527 0.929260 0.379044 0.039 Uiso 1 1 calc R U . . .
H12A H 0.409000 0.931230 0.258331 0.039 Uiso 1 1 calc R U . . .
C8 C -0.0262(4) 0.9884(3) 0.8171(3) 0.0263(6) Uani 1 1 d . . . . .
H8 H -0.041430 1.085105 0.833659 0.032 Uiso 1 1 calc R U . . .
C7 C -0.0944(4) 0.9014(4) 0.8990(3) 0.0263(6) Uani 1 1 d . . . . .
H7 H -0.155882 0.938416 0.973025 0.032 Uiso 1 1 calc R U . . .
C6 C -0.0735(4) 0.7599(4) 0.8735(3) 0.0254(6) Uani 1 1 d . . . . .
H6 H -0.121590 0.701405 0.929642 0.030 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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
O4 Cu1 N13 91.12(9) . . ?
O4 Cu1 N20 169.30(9) . . ?
N13 Cu1 N20 85.66(10) . . ?
O4 Cu1 O40 84.18(8) . . ?
N13 Cu1 O40 168.86(10) . . ?
N20 Cu1 O40 97.14(9) . . ?
O4 Cu1 O31 90.86(9) . . ?
N13 Cu1 O31 98.74(9) . . ?
N20 Cu1 O31 99.71(9) . . ?
O40 Cu1 O31 91.43(8) . . ?
O4 Cu1 O32 117.98(8) . . ?
N13 Cu1 O32 67.92(8) . . ?
N20 Cu1 O32 70.14(8) . . ?
O40 Cu1 O32 123.18(7) . . ?
O31 Cu1 O32 41.84(6) . . ?
C4 O4 Cu1 127.6(2) . . ?
Cu1 O40 H40B 120.7 . . ?
Cu1 O40 H40A 131.6 . . ?
H40B O40 H40A 107.7 . . ?
N30 O31 Cu1 122.96(16) . . ?
C9 O1 C2 121.9(2) . . ?
N30 O32 Cu1 75.51(16) . . ?
O32 N30 O33 121.7(3) . . ?
O32 N30 O31 119.7(2) . . ?
O33 N30 O31 118.6(2) . . ?
C11 N13 C14 119.1(2) . . ?
C11 N13 Cu1 128.7(2) . . ?
C14 N13 Cu1 112.21(18) . . ?
C15 N20 C19 119.0(3) . . ?
C15 N20 Cu1 112.8(2) . . ?
C19 N20 Cu1 128.09(19) . . ?
N20 C15 C16 121.8(3) . . ?
N20 C15 C14 117.5(3) . . ?
C16 C15 C14 120.7(3) . . ?
O4 C4 C3 125.4(3) . . ?
O4 C4 C10 115.2(3) . . ?
C3 C4 C10 119.4(3) . . ?
N13 C11 C3 120.9(2) . . ?
N13 C11 C12 119.0(3) . . ?
C3 C11 C12 120.1(3) . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
N13 C14 C15 111.6(2) . . ?
N13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
N13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
H14B C14 H14A 108.0 . . ?
O2 C2 O1 113.2(3) . . ?
O2 C2 C3 126.7(3) . . ?
O1 C2 C3 120.1(3) . . ?
C4 C3 C2 118.0(3) . . ?
C4 C3 C11 123.1(3) . . ?
C2 C3 C11 119.0(2) . . ?
O1 C9 C10 120.8(3) . . ?
O1 C9 C8 117.2(3) . . ?
C10 C9 C8 121.9(3) . . ?
N20 C19 C18 121.8(3) . . ?
N20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C9 C10 C5 118.4(3) . . ?
C9 C10 C4 119.3(3) . . ?
C5 C10 C4 122.2(3) . . ?
C16 C17 C18 118.8(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C6 C5 C10 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C10 C5 H5 119.7 . . ?
C19 C18 C17 119.3(3) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C11 C12 H12C 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
H12C C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?
C7 C8 C9 118.5(3) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
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
Cu1 O4 1.903(2) . ?
Cu1 N13 1.954(2) . ?
Cu1 N20 1.978(3) . ?
Cu1 O40 1.988(2) . ?
Cu1 O31 2.299(2) . ?
Cu1 O32 3.259(2) . ?
O4 C4 1.278(4) . ?
O40 H40B 0.8496 . ?
O40 H40A 0.8506 . ?
O31 N30 1.282(3) . ?
O1 C9 1.375(4) . ?
O1 C2 1.375(4) . ?
O2 C2 1.226(4) . ?
O32 N30 1.237(3) . ?
O33 N30 1.248(3) . ?
N13 C11 1.310(4) . ?
N13 C14 1.466(4) . ?
N20 C15 1.346(4) . ?
N20 C19 1.351(4) . ?
C15 C16 1.387(4) . ?
C15 C14 1.504(4) . ?
C4 C3 1.416(4) . ?
C4 C10 1.458(4) . ?
C11 C3 1.463(4) . ?
C11 C12 1.508(4) . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
C14 H14B 0.9900 . ?
C14 H14A 0.9900 . ?
C2 C3 1.450(4) . ?
C9 C10 1.387(4) . ?
C9 C8 1.390(4) . ?
C19 C18 1.380(4) . ?
C19 H19 0.9500 . ?
C10 C5 1.399(4) . ?
C17 C18 1.391(4) . ?
C17 H17 0.9500 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9500 . ?
C18 H18 0.9500 . ?
C12 H12C 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12A 0.9800 . ?
C8 C7 1.388(4) . ?
C8 H8 0.9500 . ?
C7 C6 1.395(5) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
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
_geom_hbond_publ_flag
O40 H40B O31 0.85 1.85 2.689(3) 167.3 2_566 yes
O40 H40A O2 0.85 1.93 2.729(3) 155.6 1_545 yes
C19 H19 O2 0.95 2.39 3.326(4) 170.0 1_545 yes
C8 H8 O32 0.95 2.54 3.457(4) 163.5 2_576 yes
C12 H12B O2 0.98 2.24 2.695(4) 106.7 . yes
C5 H5 O31 0.95 2.47 3.366(4) 157.2 2_566 yes
C12 H12C O33 0.98 2.50 3.473(4) 169.5 1_655 yes
C14 H14B O33 0.99 2.48 3.317(4) 141.7 1_655 yes
C17 H17 O32 0.95 2.52 3.128(4) 122.0 2_665 yes
