#------------------------------------------------------------------------------
#$Date: 2023-11-05 02:15:07 +0200 (Sun, 05 Nov 2023) $
#$Revision: 287268 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/43/7714394.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_7714394
loop_
_publ_author_name
'Moura, Fagner da Silva'
'Sobrinho, Ygor S.'
'Stellet, Carolina'
'Serna, Jilder D. P.'
'Ligiero, Carolina B. P.'
'Yoguim, Maurício I'
'Cukierman, Daphne S.'
'Diniz, Renata'
'Alves, Odivaldo C.'
'Morgon, Nelson H.'
'de Souza, Aguinaldo R.'
'Rey, Nicolás A'
_publ_section_title
;
 Copper(II) complexes of a furan-containing aroylhydrazonic ligand:
 syntheses, structural studies, solution chemistry and interaction with
 HSA.
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/d3dt02597g
_journal_year                    2023
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C13 H11 Cl Cu N2 O3, H2 O'
_chemical_formula_sum            'C13 H13 Cl Cu N2 O4'
_chemical_formula_weight         360.25
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2023-07-14 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.109(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6740(4)
_cell_length_b                   6.9206(2)
_cell_length_c                   16.1553(5)
_cell_measurement_reflns_used    14205
_cell_measurement_temperature    299.4(3)
_cell_measurement_theta_max      30.7340
_cell_measurement_theta_min      2.5140
_cell_volume                     1416.74(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-201n (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-201n (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31799
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         31.05
_diffrn_reflns_theta_min         2.52
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0348
_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)+(0.0390P)²+0.5984P] WHERE P=(FO²+2FC²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0877
_reflns_number_gt                2953
_reflns_number_total             4009
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            d3dt02597g2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7714394
_oxdiff_exptl_absorpt_empirical_full_min 0.794
_oxdiff_exptl_absorpt_empirical_full_max 1.467
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu Uani 0.35868(2) 0.67657(4) 0.43166(2) 1.000 0.0354(1) d . . .
Cl Cl Uani 0.29529(5) 0.60728(10) 0.30691(3) 1.000 0.0545(2) d . . .
O1 O Uani 0.48974(12) 0.7594(2) 0.38980(8) 1.000 0.0407(4) d . . .
O2 O Uani 0.22720(11) 0.6120(2) 0.48849(9) 1.000 0.0412(5) d . . .
O3 O Uani 0.06081(13) 0.5060(3) 0.57763(11) 1.000 0.0586(6) d . . .
N1 N Uani 0.40987(13) 0.6884(2) 0.54523(10) 1.000 0.0314(5) d . . .
N2 N Uani 0.33371(13) 0.6378(2) 0.60081(10) 1.000 0.0347(5) d . . .
C1 C Uani 0.57646(17) 0.8036(3) 0.43263(13) 1.000 0.0348(6) d . . .
C2 C Uani 0.66639(18) 0.8592(3) 0.38918(14) 1.000 0.0426(7) d . . .
C3 C Uani 0.75932(18) 0.9059(3) 0.42978(15) 1.000 0.0458(7) d . . .
C4 C Uani 0.76958(17) 0.9017(3) 0.51615(15) 1.000 0.0440(7) d . . .
O4 O Uani 0.43806(14) 0.5089(3) 0.74529(10) 1.000 0.0530(6) d G . .
C5 C Uani 0.68230(17) 0.8482(3) 0.55963(14) 1.000 0.0398(7) d . . .
C6 C Uani 0.58536(16) 0.7976(3) 0.52044(12) 1.000 0.0333(6) d . . .
C7 C Uani 0.50155(16) 0.7427(3) 0.57297(12) 1.000 0.0330(6) d . . .
C8 C Uani 0.23925(16) 0.5989(3) 0.56568(12) 1.000 0.0343(6) d . . .
C9 C Uani 0.15310(16) 0.5451(3) 0.61781(13) 1.000 0.0392(6) d . . .
C10 C Uani 0.1422(2) 0.5230(5) 0.69922(16) 1.000 0.0691(10) d . . .
C11 C Uani 0.0353(2) 0.4663(5) 0.71021(19) 1.000 0.0752(13) d . . .
C12 C Uani -0.0093(2) 0.4590(5) 0.63617(19) 1.000 0.0640(10) d . . .
C13 C Uani 0.8732(2) 0.9468(5) 0.55904(19) 1.000 0.0642(10) d . . .
H2 H Uiso 0.34557 0.63167 0.65334 1.000 0.0420 c RU . .
H2A H Uiso 0.66305 0.86467 0.33167 1.000 0.0510 c RU . .
H3 H Uiso 0.81727 0.94150 0.39879 1.000 0.0550 c RU . .
H5 H Uiso 0.68706 0.84508 0.61713 1.000 0.0480 c RU . .
H7 H Uiso 0.51332 0.74597 0.62995 1.000 0.0400 c RU . .
H10 H Uiso 0.19367 0.54084 0.74030 1.000 0.0830 c RU . .
H11 H Uiso 0.00330 0.43953 0.76023 1.000 0.0900 c RU . .
H12 H Uiso -0.07946 0.42612 0.62558 1.000 0.0770 c RU . .
H13A H Uiso 0.86193 0.96594 0.61706 1.000 0.0960 c RU . .
H13B H Uiso 0.90250 1.06215 0.53579 1.000 0.0960 c RU . .
H13C H Uiso 0.92115 0.84118 0.55161 1.000 0.0960 c RU . .
H4A H Uiso 0.45526 0.59166 0.78198 1.000 0.0790 d GU . .
H4B H Uiso 0.49561 0.45281 0.73382 1.000 0.0790 d GU . .
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'
Cu Cu 0.3201 1.2651 ' 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_
_exptl_absorpt_coefficient_mu
1.746
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0071
-1 0 0 0.0328
0 0 1 0.0312
0 0 -1 0.0225
0 1 0 0.0957
0 -1 0 0.1066
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl Cu O1 92.63(4) . . . yes
Cl Cu O2 94.59(5) . . . yes
Cl Cu N1 169.63(5) . . . yes
O1 Cu O2 172.21(6) . . . yes
O1 Cu N1 92.61(6) . . . yes
O2 Cu N1 80.73(7) . . . yes
Cu O1 C1 127.48(13) . . . yes
Cu O2 C8 113.04(13) . . . yes
C9 O3 C12 106.65(19) . . . yes
Cu N1 N2 112.41(12) . . . yes
Cu N1 C7 128.55(14) . . . yes
N2 N1 C7 118.99(16) . . . yes
N1 N2 C8 113.97(16) . . . yes
O1 C1 C2 118.43(19) . . . yes
O1 C1 C6 124.34(19) . . . yes
C2 C1 C6 117.23(19) . . . no
C1 C2 C3 121.5(2) . . . no
N1 N2 H2 123.00 . . . no
C8 N2 H2 123.00 . . . no
C2 C3 C4 122.2(2) . . . no
C3 C4 C13 121.2(2) . . . no
C3 C4 C5 117.1(2) . . . no
C5 C4 C13 121.7(2) . . . no
C4 C5 C6 122.6(2) . . . no
C1 C6 C7 123.84(19) . . . no
C5 C6 C7 116.78(18) . . . no
C1 C6 C5 119.38(19) . . . no
N1 C7 C6 123.14(18) . . . yes
O2 C8 C9 121.32(18) . . . yes
O2 C8 N2 119.70(18) . . . yes
N2 C8 C9 118.98(17) . . . yes
O3 C9 C10 110.2(2) . . . yes
C8 C9 C10 134.4(2) . . . no
O3 C9 C8 115.39(18) . . . yes
C9 C10 C11 105.7(2) . . . no
C10 C11 C12 106.9(3) . . . no
O3 C12 C11 110.6(2) . . . yes
C1 C2 H2A 119.00 . . . no
C3 C2 H2A 119.00 . . . no
C2 C3 H3 119.00 . . . no
C4 C3 H3 119.00 . . . no
H4A O4 H4B 104.00 . . . no
C4 C5 H5 119.00 . . . no
C6 C5 H5 119.00 . . . no
C6 C7 H7 118.00 . . . no
N1 C7 H7 118.00 . . . no
C9 C10 H10 127.00 . . . no
C11 C10 H10 127.00 . . . no
C12 C11 H11 127.00 . . . no
C10 C11 H11 127.00 . . . no
O3 C12 H12 125.00 . . . no
C11 C12 H12 125.00 . . . no
C4 C13 H13B 109.00 . . . no
C4 C13 H13C 109.00 . . . no
C4 C13 H13A 109.00 . . . no
H13A C13 H13C 109.00 . . . no
H13B C13 H13C 109.00 . . . no
H13A C13 H13B 109.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu Cl 2.2078(6) . . yes
Cu O1 1.8943(15) . . yes
Cu O2 1.9694(14) . . yes
Cu N1 1.9359(17) . . yes
O1 C1 1.323(3) . . yes
O2 C8 1.257(2) . . yes
O3 C9 1.354(3) . . yes
O3 C12 1.350(3) . . yes
N1 N2 1.376(2) . . yes
N1 C7 1.293(3) . . yes
N2 C8 1.342(3) . . yes
C1 C2 1.404(3) . . no
C1 C6 1.422(3) . . no
C2 C3 1.376(3) . . no
N2 H2 0.8600 . . no
C3 C4 1.399(3) . . no
C4 C5 1.373(3) . . no
C4 C13 1.506(3) . . no
C5 C6 1.415(3) . . no
C6 C7 1.424(3) . . no
C8 C9 1.441(3) . . no
C9 C10 1.334(3) . . no
C10 C11 1.425(4) . . no
C11 C12 1.314(4) . . no
C2 H2A 0.9300 . . no
C3 H3 0.9300 . . no
O4 H4A 0.8500 . . no
O4 H4B 0.8500 . . no
C5 H5 0.9300 . . no
C7 H7 0.9300 . . no
C10 H10 0.9300 . . no
C11 H11 0.9300 . . no
C12 H12 0.9300 . . no
C13 H13C 0.9600 . . no
C13 H13A 0.9600 . . no
C13 H13B 0.9600 . . no
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
N2 H2 O4 0.8600 2.0600 2.806(2) 145.00 . yes
O4 H4A O1 0.8500 2.0600 2.897(2) 167.00 4_565 yes
O4 H4B Cl 0.8500 2.7700 3.5901(19) 161.00 3_666 yes
O4 H4B O1 0.8500 2.4900 3.021(2) 121.00 3_666 yes
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
Cl Cu O1 C1 -171.24(16) . . . . no
N1 Cu O1 C1 -0.19(16) . . . . no
Cl Cu O2 C8 167.03(13) . . . . no
N1 Cu O2 C8 -3.64(14) . . . . no
O1 Cu N1 N2 179.27(11) . . . . no
O1 Cu N1 C7 2.00(17) . . . . no
O2 Cu N1 N2 3.32(11) . . . . no
O2 Cu N1 C7 -173.94(17) . . . . no
Cu O1 C1 C2 178.95(14) . . . . no
Cu O1 C1 C6 -0.7(3) . . . . no
Cu O2 C8 N2 3.3(2) . . . . no
Cu O2 C8 C9 -177.47(15) . . . . no
C12 O3 C9 C8 180.0(2) . . . . no
C12 O3 C9 C10 0.2(3) . . . . no
C9 O3 C12 C11 -0.3(3) . . . . no
Cu N1 N2 C8 -2.65(18) . . . . no
C7 N1 N2 C8 174.91(17) . . . . no
Cu N1 C7 C6 -3.0(3) . . . . no
N2 N1 C7 C6 179.94(17) . . . . no
N1 N2 C8 O2 -0.5(3) . . . . no
N1 N2 C8 C9 -179.71(16) . . . . no
O1 C1 C2 C3 -179.60(19) . . . . no
C6 C1 C2 C3 0.0(3) . . . . no
O1 C1 C6 C5 -180.0(2) . . . . no
O1 C1 C6 C7 0.1(3) . . . . no
C2 C1 C6 C5 0.4(3) . . . . no
C2 C1 C6 C7 -179.5(2) . . . . no
C1 C2 C3 C4 -0.3(3) . . . . no
C2 C3 C4 C5 0.1(3) . . . . no
C2 C3 C4 C13 177.9(2) . . . . no
C3 C4 C5 C6 0.4(3) . . . . no
C13 C4 C5 C6 -177.4(2) . . . . no
C4 C5 C6 C1 -0.7(3) . . . . no
C4 C5 C6 C7 179.3(2) . . . . no
C1 C6 C7 N1 1.8(3) . . . . no
C5 C6 C7 N1 -178.17(19) . . . . no
O2 C8 C9 O3 1.5(3) . . . . no
O2 C8 C9 C10 -178.8(3) . . . . no
N2 C8 C9 O3 -179.26(18) . . . . no
N2 C8 C9 C10 0.4(4) . . . . no
O3 C9 C10 C11 -0.1(3) . . . . no
C8 C9 C10 C11 -179.8(3) . . . . no
C9 C10 C11 C12 -0.1(4) . . . . no
C10 C11 C12 O3 0.3(4) . . . . no
