#------------------------------------------------------------------------------
#$Date: 2021-06-30 12:39:51 +0300 (Wed, 30 Jun 2021) $
#$Revision: 266810 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/37/1563796.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_1563796
loop_
_publ_author_name
'Alvarez, Natalia'
'Mendes, Luis F.S.'
'Kramer, M. Gabriela'
'Torre, María H.'
'Costa-Filho, Antonio J.'
'Ellena, Javier'
'Facchin, Gianella'
_publ_section_title
;
 Development of copper(II)-diimine-iminodiacetate mixed ligand complexes
 as potential antitumor agents
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              61
_journal_page_last               70
_journal_paper_doi               10.1016/j.ica.2018.07.052
_journal_volume                  483
_journal_year                    2018
_chemical_formula_sum            'C17 H19 Cu N3 O6'
_chemical_formula_weight         424.89
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 130.530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.310(7)
_cell_length_b                   17.940(6)
_cell_length_c                   14.663(9)
_cell_measurement_reflns_used    8574
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.9777
_cell_measurement_theta_min      3.6766
_cell_volume                     4261(3)
_computing_cell_refinement       'APEX2 v2014.5-0 (Bruker AXS)'
_computing_data_collection       'APEX2 v2014.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'BRUKER D8 venture diffractometer'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.915
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12630
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.446
_diffrn_reflns_theta_min         3.677
_diffrn_source                   'microfocused sealed tube'
_diffrn_source_type              'INCOATEC ICT-IMSB-HOUSING-L model D21502'
_exptl_absorpt_coefficient_mu    1.756
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       prism
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.105
_platon_squeeze_details
;
Crystallization was performed in water. 
The resulting electron density was largely uninterpretable, 
so it was removed with SQUEEZE in Platon (Spek, 2009).
Electron count and volume are consistent with 8 water molecules per void,
meaning two extra water molecules per assymetric unit. 
Also consistent with experimental elemental analysis of the sample.
;
_refine_diff_density_max         1.149
_refine_diff_density_min         -1.142
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.310
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.310
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0952
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2982
_refine_ls_wR_factor_ref         0.3158
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2767
_reflns_number_total             3556
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mmc4.cif
_cod_data_source_block           cu_ida_4met_0ma_a_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8369 2020-08-20 11:38:08Z andrius 
;
_cod_original_cell_volume        4260(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1563796
_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.
;
_platon_squeeze_void_probe_radius 1.20
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
Cu1 Cu 0.38453(5) 0.45571(4) 0.09714(6) 0.0580(4) Uani 1 1 d . . . . .
N1 N 0.3321(3) 0.3906(2) 0.1444(3) 0.0583(11) Uani 1 1 d . . . . .
C1 C 0.2857(4) 0.4087(3) 0.1740(5) 0.0684(15) Uani 1 1 d . . . . .
H1 H 0.2765 0.4600 0.1783 0.082 Uiso 1 1 calc R U . . .
O1 O 0.2914(2) 0.46062(19) -0.1032(3) 0.0628(10) Uani 1 1 d . . . . .
O2 O 0.1656(2) 0.5076(2) -0.2416(3) 0.0770(12) Uani 1 1 d . . . . .
N2 N 0.4292(3) 0.3578(3) 0.0979(4) 0.0640(12) Uani 1 1 d . . . . .
C2 C 0.2511(4) 0.3559(3) 0.1981(5) 0.0725(15) Uani 1 1 d . . . . .
H2 H 0.2185 0.3709 0.2179 0.087 Uiso 1 1 calc R U . . .
O4 O 0.4713(3) 0.5132(3) 0.1232(4) 0.0787(12) Uani 1 1 d . . . . .
C4 C 0.3117(3) 0.2602(3) 0.1629(4) 0.0665(15) Uani 1 1 d . . . . .
O3 O 0.5084(3) 0.6280(3) 0.1275(6) 0.1099(18) Uani 1 1 d . . . . .
N3 N 0.3276(3) 0.5530(2) 0.0702(4) 0.0581(11) Uani 1 1 d . . . . .
H3 H 0.3290 0.5627 0.1386 0.070 Uiso 1 1 calc R U . . .
C3 C 0.2643(4) 0.2807(4) 0.1932(5) 0.084(2) Uani 1 1 d . . . . .
H3A H 0.2414 0.2437 0.2104 0.101 Uiso 1 1 calc R U . . .
C5 C 0.3306(4) 0.1849(4) 0.1534(6) 0.091(2) Uani 1 1 d . . . . .
H5 H 0.3087 0.1449 0.1676 0.109 Uiso 1 1 calc R U . . .
O3W O 0.0174(4) 0.4382(6) 0.1751(6) 0.129(3) Uani 0.75 1 d . . P . .
H301 H 0.0603 0.4280 0.1844 0.193 Uiso 0.75 1 d R U P . .
H302 H 0.0276 0.4272 0.2400 0.193 Uiso 0.75 1 d R U P . .
C6 C 0.3769(4) 0.1690(4) 0.1260(6) 0.090(2) Uani 1 1 d . . . . .
H6 H 0.3873 0.1183 0.1214 0.107 Uiso 1 1 calc R U . . .
C7 C 0.4120(4) 0.2263(3) 0.1029(5) 0.078(2) Uani 1 1 d . . . . .
C8 C 0.4619(5) 0.2122(5) 0.0738(6) 0.093(3) Uani 1 1 d . . . . .
C9 C 0.4939(4) 0.2714(6) 0.0596(6) 0.096(3) Uani 1 1 d . . . . .
H9 H 0.5287 0.2635 0.0414 0.116 Uiso 1 1 calc R U . . .
C17 C 0.4581(4) 0.5822(4) 0.1101(6) 0.0745(16) Uani 1 1 d . . . . .
C16 C 0.3762(4) 0.6104(4) 0.0684(6) 0.0715(15) Uani 1 1 d . . . . .
H16A H 0.3865 0.6523 0.1206 0.086 Uiso 1 1 calc R U . . .
H16B H 0.3434 0.6298 -0.0143 0.086 Uiso 1 1 calc R U . . .
C15 C 0.2412(4) 0.5481(3) -0.0423(5) 0.0586(13) Uani 1 1 d . . . . .
H15A H 0.2195 0.5990 -0.0735 0.070 Uiso 1 1 calc R U . . .
H15B H 0.2074 0.5247 -0.0257 0.070 Uiso 1 1 calc R U . . .
C14 C 0.2332(3) 0.5027(3) -0.1371(4) 0.0520(11) Uani 1 1 d . . . . .
C13 C 0.4770(6) 0.1334(6) 0.0559(11) 0.165(6) Uani 1 1 d . . . . .
H13A H 0.4267 0.1138 -0.0200 0.247 Uiso 1 1 calc R U . . .
H13B H 0.4921 0.1021 0.1223 0.247 Uiso 1 1 calc R U . . .
H13C H 0.5220 0.1332 0.0537 0.247 Uiso 1 1 calc R U . . .
C12 C 0.3453(3) 0.3176(3) 0.1411(4) 0.0619(14) Uani 1 1 d . . . . .
C11 C 0.3971(3) 0.3002(3) 0.1121(4) 0.0647(16) Uani 1 1 d . . . . .
C10 C 0.4763(4) 0.3454(4) 0.0717(5) 0.0754(18) Uani 1 1 d . . . . .
H10 H 0.4990 0.3863 0.0605 0.090 Uiso 1 1 calc R U . . .
O2W O 0.3645(4) 0.0468(4) 0.4471(6) 0.089(2) Uani 0.75 1 d . . P . .
H201 H 0.3692 0.0519 0.3941 0.134 Uiso 0.75 1 d R U P . .
H2O2 H 0.4075 0.0245 0.5067 0.134 Uiso 0.75 1 d R U P . .
O1W O 0.1678(4) 0.1003(3) 0.2335(4) 0.0461(14) Uani 0.5 1 d . . P . .
H1O1 H 0.1748 0.0850 0.1859 0.069 Uiso 0.5 1 d R U P . .
H102 H 0.2133 0.0955 0.3046 0.069 Uiso 0.5 1 d R U P . .
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
O4 Cu1 N2 94.40(19) . .
O4 Cu1 N3 87.31(19) . .
N2 Cu1 N3 171.64(17) . .
O4 Cu1 N1 155.95(18) . .
N2 Cu1 N1 81.8(2) . .
N3 Cu1 N1 99.89(18) . .
O4 Cu1 O1 99.07(18) . .
N2 Cu1 O1 93.16(15) . .
N3 Cu1 O1 78.49(15) . .
N1 Cu1 O1 104.83(16) . .
C12 N1 C1 117.4(5) . .
C12 N1 Cu1 111.9(4) . .
C1 N1 Cu1 130.7(4) . .
N1 C1 C2 122.7(6) . .
N1 C1 H1 118.6 . .
C2 C1 H1 118.6 . .
C14 O1 Cu1 110.5(3) . .
C10 N2 C11 119.1(5) . .
C10 N2 Cu1 127.2(5) . .
C11 N2 Cu1 113.2(4) . .
C1 C2 C3 119.5(6) . .
C1 C2 H2 120.2 . .
C3 C2 H2 120.2 . .
C17 O4 Cu1 113.9(4) . .
C3 C4 C12 117.6(5) . .
C3 C4 C5 125.8(6) . .
C12 C4 C5 116.6(6) . .
C16 N3 C15 113.9(4) . .
C16 N3 Cu1 105.6(4) . .
C15 N3 Cu1 108.9(3) . .
C16 N3 H3 109.5 . .
C15 N3 H3 109.5 . .
Cu1 N3 H3 109.5 . .
C2 C3 C4 119.1(6) . .
C2 C3 H3A 120.4 . .
C4 C3 H3A 120.4 . .
C6 C5 C4 123.0(7) . .
C6 C5 H5 118.5 . .
C4 C5 H5 118.5 . .
H301 O3W H302 107.7 . .
C5 C6 C7 121.8(6) . .
C5 C6 H6 119.1 . .
C7 C6 H6 119.1 . .
C11 C7 C8 118.0(7) . .
C11 C7 C6 118.2(7) . .
C8 C7 C6 123.8(6) . .
C9 C8 C7 117.6(6) . .
C9 C8 C13 121.6(9) . .
C7 C8 C13 120.8(10) . .
C8 C9 C10 121.1(8) . .
C8 C9 H9 119.5 . .
C10 C9 H9 119.5 . .
O3 C17 O4 123.0(7) . .
O3 C17 C16 118.6(7) . .
O4 C17 C16 118.4(6) . .
N3 C16 C17 113.5(5) . .
N3 C16 H16A 108.9 . .
C17 C16 H16A 108.9 . .
N3 C16 H16B 108.9 . .
C17 C16 H16B 108.9 . .
H16A C16 H16B 107.7 . .
N3 C15 C14 111.7(4) . .
N3 C15 H15A 109.3 . .
C14 C15 H15A 109.3 . .
N3 C15 H15B 109.3 . .
C14 C15 H15B 109.3 . .
H15A C15 H15B 107.9 . .
O1 C14 O2 125.9(5) . .
O1 C14 C15 117.9(4) . .
O2 C14 C15 116.0(5) . .
C8 C13 H13A 109.5 . .
C8 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C8 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
N1 C12 C4 123.6(6) . .
N1 C12 C11 116.0(6) . .
C4 C12 C11 120.4(5) . .
N2 C11 C7 123.6(6) . .
N2 C11 C12 116.4(5) . .
C7 C11 C12 120.0(7) . .
N2 C10 C9 120.7(8) . .
N2 C10 H10 119.6 . .
C9 C10 H10 119.6 . .
H201 O2W H2O2 107.7 . .
H1O1 O1W H102 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O4 1.927(5) .
Cu1 N2 1.994(4) .
Cu1 N3 2.012(4) .
Cu1 N1 2.025(5) .
Cu1 O1 2.236(4) .
N1 C12 1.346(7) .
N1 C1 1.352(7) .
C1 C2 1.380(9) .
C1 H1 0.9500 .
O1 C14 1.247(6) .
O2 C14 1.250(6) .
N2 C10 1.306(8) .
N2 C11 1.330(8) .
C2 C3 1.391(10) .
C2 H2 0.9500 .
O4 C17 1.257(9) .
C4 C3 1.390(10) .
C4 C12 1.406(9) .
C4 C5 1.443(10) .
O3 C17 1.238(8) .
N3 C16 1.472(8) .
N3 C15 1.474(7) .
N3 H3 1.0000 .
C3 H3A 0.9500 .
C5 C6 1.314(11) .
C5 H5 0.9500 .
O3W H301 0.8500 .
O3W H302 0.8500 .
C6 C7 1.436(12) .
C6 H6 0.9500 .
C7 C11 1.389(8) .
C7 C8 1.403(11) .
C8 C9 1.349(13) .
C8 C13 1.510(11) .
C9 C10 1.422(10) .
C9 H9 0.9500 .
C17 C16 1.513(9) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C15 C14 1.521(7) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C12 C11 1.450(8) .
C10 H10 0.9500 .
O2W H201 0.8500 .
O2W H2O2 0.8499 .
O1W H1O1 0.8499 .
O1W H102 0.8500 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.630 0.250 -0.120 320 87 '8 (H2 O)'
2 0.130 0.750 -0.120 320 87 '8 (H2 O)'
