#------------------------------------------------------------------------------
#$Date: 2020-11-06 13:55:43 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258782 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/56/7705673.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_7705673
loop_
_publ_author_name
'Rigamonti, Luca'
'Reginato, Francesco'
'Ferrari, Erika'
'Pigani, Laura'
'Gigli, Lara'
'Demitri, Nicola'
'Kopel, Pavel'
'Tesarova, Barbora'
'Heger, Zbynek'
_publ_section_title
;
 From solid state to in vitro anticancer activity of copper(II)
 compounds with electronically-modulated NNO Schiff base ligands.
;
_journal_issue                   41
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14626
_journal_page_last               14639
_journal_paper_doi               10.1039/d0dt03038d
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C10 H13 Cl Cu N2 O2'
_chemical_formula_sum            'C10 H13 Cl Cu N2 O2'
_chemical_formula_weight         292.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc24072h
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-09-23 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.38(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.252(3)
_cell_length_b                   7.9730(16)
_cell_length_c                   10.332(2)
_cell_measurement_reflns_used    3560
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.226
_cell_measurement_theta_min      1.253
_cell_volume                     1120.4(4)
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_molecular_graphics    'Ortep3 for Windows - Coot'
_computing_publication_material  'enCIFer - publCIF'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19085
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.779
_diffrn_reflns_theta_min         1.475
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_exptl_absorpt_coefficient_mu    2.009
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_description       'Thin plates'
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.154
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.144
_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     147
_refine_ls_number_reflns         3246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0389
_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)+(0.0582P)²+3.2099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3080
_reflns_number_total             3246
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt03038d2.cif
_cod_data_source_block           Cu1
_cod_depositor_comments
'Adding full bibliography for 7705671--7705674.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7705673
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.824
_shelx_estimated_absorpt_t_max   0.961
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cu1 Cu 0.60320(2) 0.59343(4) 0.56684(3) 0.01235(10) Uani 1 1 d . . . . .
Cl1 Cl 0.46351(4) 0.73667(8) 0.46505(6) 0.01561(13) Uani 1 1 d . . . . .
O1 O 0.63646(14) 0.5851(2) 0.40015(19) 0.0144(3) Uani 1 1 d . . . . .
N1 N 0.57345(18) 0.5885(3) 0.7443(2) 0.0164(4) Uani 1 1 d . . . . .
H10 H 0.572382 0.694793 0.775974 0.020 Uiso 1 1 calc R U . . .
H11 H 0.513473 0.541177 0.733326 0.020 Uiso 1 1 calc R U . . .
N2 N 0.73594(16) 0.5330(3) 0.6763(2) 0.0149(4) Uani 1 1 d . . . . .
O2 O 0.96378(15) 0.3116(3) 0.2944(2) 0.0209(4) Uani 1 1 d . . . . .
C2 C 0.72186(19) 0.4947(3) 0.2500(3) 0.0154(4) Uani 1 1 d . . . . .
H1 H 0.667937 0.529339 0.175743 0.019 Uiso 1 1 calc R U . . .
C7 C 0.80406(19) 0.4741(3) 0.6325(3) 0.0156(5) Uani 1 1 d . . . . .
H5 H 0.862830 0.437741 0.697730 0.019 Uiso 1 1 calc R U . . .
C1 C 0.71612(18) 0.5147(3) 0.3842(3) 0.0131(4) Uani 1 1 d . . . . .
C9 C 0.6502(2) 0.4897(4) 0.8414(3) 0.0184(5) Uani 1 1 d . . . . .
H8 H 0.638302 0.368302 0.823871 0.022 Uiso 1 1 calc R U . . .
H9 H 0.650132 0.513668 0.935386 0.022 Uiso 1 1 calc R U . . .
C8 C 0.7481(2) 0.5395(4) 0.8225(3) 0.0176(5) Uani 1 1 d . . . . .
H7 H 0.766514 0.654225 0.857648 0.021 Uiso 1 1 calc R U . . .
H6 H 0.800403 0.461066 0.871884 0.021 Uiso 1 1 calc R U . . .
C3 C 0.8036(2) 0.4266(3) 0.2245(3) 0.0163(5) Uani 1 1 d . . . . .
H2 H 0.804911 0.415066 0.133595 0.020 Uiso 1 1 calc R U . . .
C5 C 0.88153(19) 0.3874(3) 0.4631(3) 0.0156(5) Uani 1 1 d . . . . .
H4 H 0.935278 0.348576 0.535773 0.019 Uiso 1 1 calc R U . . .
C6 C 0.79827(18) 0.4588(3) 0.4908(2) 0.0135(4) Uani 1 1 d . . . . .
C4 C 0.88488(19) 0.3739(3) 0.3315(3) 0.0166(5) Uani 1 1 d . . . . .
C10 C 1.0330(2) 0.2134(4) 0.3938(3) 0.0231(6) Uani 1 1 d . . . . .
H12 H 1.064786 0.283562 0.472538 0.035 Uiso 1 1 calc R U . . .
H13 H 1.082840 0.169110 0.354974 0.035 Uiso 1 1 calc R U . . .
H14 H 0.998858 0.120082 0.422040 0.035 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 0.0030 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1460 0.1544 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3262 1.2361 '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
O1 Cu1 N2 93.15(9) . . ?
O1 Cu1 N1 176.32(9) . . ?
N2 Cu1 N1 84.16(10) . . ?
O1 Cu1 Cl1 91.11(6) . . ?
N2 Cu1 Cl1 163.59(7) . . ?
N1 Cu1 Cl1 92.17(7) . . ?
C1 O1 Cu1 125.36(17) . . ?
C9 N1 Cu1 108.47(17) . . ?
C7 N2 C8 120.6(2) . . ?
C7 N2 Cu1 126.38(19) . . ?
C8 N2 Cu1 112.54(17) . . ?
C4 O2 C10 116.2(2) . . ?
C3 C2 C1 121.8(2) . . ?
N2 C7 C6 124.8(2) . . ?
O1 C1 C6 125.3(2) . . ?
O1 C1 C2 118.1(2) . . ?
C6 C1 C2 116.6(2) . . ?
N1 C9 C8 107.2(2) . . ?
N2 C8 C9 107.0(2) . . ?
C2 C3 C4 120.8(2) . . ?
C4 C5 C6 120.5(2) . . ?
C1 C6 C5 121.0(2) . . ?
C1 C6 C7 122.9(2) . . ?
C5 C6 C7 116.0(2) . . ?
C5 C4 O2 124.8(3) . . ?
C5 C4 C3 119.3(2) . . ?
O2 C4 C3 115.9(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
Cu1 O1 1.9191(19) . ?
Cu1 N2 1.952(2) . ?
Cu1 N1 2.002(2) . ?
Cu1 Cl1 2.2633(9) . ?
Cu1 Cl1 2.7842(9) 3_666 ?
O1 C1 1.320(3) . ?
N1 C9 1.473(4) . ?
N2 C7 1.277(3) . ?
N2 C8 1.469(3) . ?
O2 C4 1.384(3) . ?
O2 C10 1.426(4) . ?
C2 C3 1.380(4) . ?
C2 C1 1.423(3) . ?
C7 C6 1.447(3) . ?
C1 C6 1.418(3) . ?
C9 C8 1.518(4) . ?
C3 C4 1.405(4) . ?
C5 C4 1.379(4) . ?
C5 C6 1.420(3) . ?
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
N1 H10 Cl1 0.91 2.89 3.426(3) 119.3 4_576 yes
N1 H10 O1 0.91 2.20 3.051(3) 154.4 4_576 yes
N1 H11 O1 0.91 2.39 3.229(3) 152.9 3_666 yes
C7 H5 O2 0.95 2.48 3.301(3) 144.3 4_566 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
C8 N2 C7 C6 178.5(2) . . . . ?
Cu1 N2 C7 C6 7.2(4) . . . . ?
Cu1 O1 C1 C6 -11.3(4) . . . . ?
Cu1 O1 C1 C2 169.73(18) . . . . ?
C3 C2 C1 O1 178.2(2) . . . . ?
C3 C2 C1 C6 -0.8(4) . . . . ?
Cu1 N1 C9 C8 42.2(2) . . . . ?
C7 N2 C8 C9 -139.5(3) . . . . ?
Cu1 N2 C8 C9 32.9(3) . . . . ?
N1 C9 C8 N2 -48.6(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
O1 C1 C6 C5 -178.8(2) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
O1 C1 C6 C7 -0.3(4) . . . . ?
C2 C1 C6 C7 178.6(2) . . . . ?
C4 C5 C6 C1 1.3(4) . . . . ?
C4 C5 C6 C7 -177.2(2) . . . . ?
N2 C7 C6 C1 2.5(4) . . . . ?
N2 C7 C6 C5 -179.0(3) . . . . ?
C6 C5 C4 O2 177.7(2) . . . . ?
C6 C5 C4 C3 -2.1(4) . . . . ?
C10 O2 C4 C5 18.2(4) . . . . ?
C10 O2 C4 C3 -162.0(2) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C2 C3 C4 O2 -178.3(2) . . . . ?
