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#$Date: 2023-07-04 03:14:38 +0300 (Tue, 04 Jul 2023) $
#$Revision: 284764 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/25/7062536.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_7062536
loop_
_publ_author_name
'Nonkuntod, Prangtip'
'Boonmak, Jaursup'
'Senawong, Thanaset'
'Soikum, Chaiyaporn'
'Chaveerach, Prapansak'
'Watwiangkham, Athis'
'Suthirakun, Suwit'
'Chaveerach, Unchulee'
_publ_section_title
;
 The effect of gallic acid on the copper(ii) complex of
 N-(methylpyridin-2-yl)-amidino-O-methylurea: crystal structure, DNA
 interactions, in vitro cytotoxicity and antibacterial activity
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12259
_journal_page_last               12273
_journal_paper_doi               10.1039/D3NJ00446E
_journal_volume                  47
_journal_year                    2023
_chemical_formula_sum            'C32 H46 Cl2 Cu2 N10 O17'
_chemical_formula_weight         1040.77
_chemical_name_systematic
'3,4,5-trihydroxybenzoato-N-methyl(pyridine-2-yl)cyanoguanidinecopper(II)chloride trihydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-08-25 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.0320(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.3859(5)
_cell_length_b                   6.7939(2)
_cell_length_c                   25.8663(9)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.984
_cell_measurement_theta_min      3.106
_cell_volume                     2120.55(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       BrukerAPEX2
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker D8 QUEST PHOTON 100
;
_diffrn_measurement_method       '\fandω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            43596
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.105
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.213
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4174
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0496P)²+1.7900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3182
_reflns_number_total             4174
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj00446e2.cif
_cod_data_source_block           326J2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7062536
_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.
;
_shelx_estimated_absorpt_t_min   0.820
_shelx_estimated_absorpt_t_max   0.942
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.0195(3) 0.4689(5) 0.73342(11) 0.0461(8) Uani 1 1 d . . . . .
H1 H 0.0789 0.4643 0.7170 0.055 Uiso 1 1 calc R U . . .
C2 C -0.0833(3) 0.5130(6) 0.70385(14) 0.0614(10) Uani 1 1 d . . . . .
H2 H -0.0938 0.5381 0.6677 0.074 Uiso 1 1 calc R U . . .
C3 C -0.1713(3) 0.5200(6) 0.72798(15) 0.0664(11) Uani 1 1 d . . . . .
H3 H -0.2421 0.5494 0.7084 0.080 Uiso 1 1 calc R U . . .
C4 C -0.1530(3) 0.4829(6) 0.78155(15) 0.0559(9) Uani 1 1 d . . . . .
H4 H -0.2114 0.4884 0.7987 0.067 Uiso 1 1 calc R U . . .
C5 C -0.0479(2) 0.4378(4) 0.80949(12) 0.0385(7) Uani 1 1 d . . . . .
C6 C -0.0228(2) 0.3946(4) 0.86772(12) 0.0390(7) Uani 1 1 d . . . . .
H6A H -0.0447 0.5056 0.8866 0.047 Uiso 1 1 calc R U . . .
H6B H -0.0647 0.2804 0.8743 0.047 Uiso 1 1 calc R U . . .
C7 C 0.1288(2) 0.3135(4) 0.93665(11) 0.0362(7) Uani 1 1 d . . . . .
H7B H 0.265(3) 0.164(3) 0.4347(13) 0.17(3) Uiso 1 1 d D . . . .
H7A H 0.299(3) 0.3748(13) 0.4484(13) 0.087(17) Uiso 1 1 d D . . . .
C8 C 0.3257(2) 0.2829(5) 0.93459(11) 0.0370(7) Uani 1 1 d . . . . .
H8B H 0.038(2) 0.140(3) 0.6367(8) 0.088(14) Uiso 1 1 d D . . . .
H8A H -0.0500(4) 0.243(5) 0.5955(12) 0.107(17) Uiso 1 1 d D . . . .
C9 C 0.5211(3) 0.2384(7) 0.95349(14) 0.0649(11) Uani 1 1 d . . . . .
H9A H 0.5148 0.1429 0.9256 0.097 Uiso 1 1 calc R U . . .
H9B H 0.5798 0.2009 0.9829 0.097 Uiso 1 1 calc R U . . .
H9C H 0.5371 0.3651 0.9406 0.097 Uiso 1 1 calc R U . . .
C10 C 0.3510(2) 0.4200(4) 0.76983(11) 0.0344(7) Uani 1 1 d . . . . .
H10B H 0.686(3) 0.5662(16) 0.8732(13) 0.016(12) Uiso 0.5 1 d D . P . .
H10A H 0.605(2) 0.445(4) 0.8326(10) 0.042(17) Uiso 0.5 1 d D . P . .
C11 C 0.3705(2) 0.4018(4) 0.71440(10) 0.0311(6) Uani 1 1 d . . . . .
C12 C 0.4758(2) 0.4282(4) 0.70591(11) 0.0335(6) Uani 1 1 d . . . . .
H12 H 0.5337 0.4651 0.7338 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4947(2) 0.3994(4) 0.65575(11) 0.0335(6) Uani 1 1 d . . . . .
C14 C 0.4093(2) 0.3498(4) 0.61355(11) 0.0318(6) Uani 1 1 d . . . . .
C15 C 0.3028(2) 0.3286(4) 0.62185(11) 0.0324(6) Uani 1 1 d . . . . .
C16 C 0.2839(2) 0.3520(4) 0.67204(11) 0.0333(6) Uani 1 1 d . . . . .
H16 H 0.2129 0.3343 0.6776 0.040 Uiso 1 1 calc R U . . .
N1 N 0.03755(19) 0.4315(3) 0.78598(9) 0.0355(6) Uani 1 1 d . . . . .
N2 N 0.09473(19) 0.3573(3) 0.88688(9) 0.0336(5) Uani 1 1 d . . . . .
N3 N 0.2388(2) 0.2779(4) 0.95854(9) 0.0416(6) Uani 1 1 d . . . . .
H3B H 0.2547 0.2486 0.9917 0.050 Uiso 1 1 calc R U . . .
N4 N 0.31588(19) 0.3158(4) 0.88541(9) 0.0380(6) Uani 1 1 d . . . . .
H4B H 0.3760 0.3122 0.8741 0.046 Uiso 1 1 calc R U . . .
N5 N 0.0638(2) 0.3008(4) 0.97134(10) 0.0485(7) Uani 1 1 d . . . . .
H5A H -0.0062 0.3225 0.9611 0.058 Uiso 1 1 calc R U . . .
H5B H 0.0919 0.2710 1.0039 0.058 Uiso 1 1 calc R U . . .
O1 O 0.25300(16) 0.3815(3) 0.77396(7) 0.0418(5) Uani 1 1 d . . . . .
O2 O 0.42911(17) 0.4649(4) 0.80708(8) 0.0502(6) Uani 1 1 d . . . . .
O3 O 0.60047(17) 0.4239(4) 0.64955(9) 0.0498(6) Uani 1 1 d . . . . .
H3A H 0.6043(9) 0.388(6) 0.6234(16) 0.075 Uiso 1 1 calc R U . . .
O4 O 0.43423(18) 0.3226(4) 0.56522(8) 0.0453(6) Uani 1 1 d . . . . .
H4A H 0.385(3) 0.299(6) 0.5459(11) 0.068 Uiso 1 1 calc R U . . .
O5 O 0.22182(18) 0.2851(4) 0.57768(7) 0.0465(6) Uani 1 1 d . . . . .
H5 H 0.162(3) 0.261(6) 0.5867(5) 0.070 Uiso 1 1 calc R U . . .
O6 O 0.41838(18) 0.2477(4) 0.97057(8) 0.0541(6) Uani 1 1 d . . . . .
O7 O 0.3169(3) 0.2416(6) 0.45940(13) 0.0900(10) Uani 1 1 d D . . . .
O8 O 0.0287(2) 0.2322(4) 0.60788(10) 0.0650(7) Uani 1 1 d D . . . .
O9 O 0.6674(4) 0.4334(7) 0.86223(19) 0.0517(12) Uani 0.5 1 d D . P . .
Cl1 Cl 0.7490(4) 0.246(3) 0.57938(17) 0.062(3) Uani 0.41(2) 1 d . . P A 2
Cl1A Cl 0.7659(4) 0.3512(17) 0.57759(10) 0.0520(15) Uani 0.59(2) 1 d . . P A 1
Cu1 Cu 0.18256(3) 0.37265(5) 0.83335(2) 0.03177(13) 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'
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'
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'
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
N1 C1 C2 121.9(3) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 121.5(3) . . ?
N1 C5 C6 116.5(3) . . ?
C4 C5 C6 122.0(3) . . ?
N2 C6 C5 110.0(2) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 N5 124.8(3) . . ?
N2 C7 N3 121.4(3) . . ?
N5 C7 N3 113.8(3) . . ?
N4 C8 O6 127.3(3) . . ?
N4 C8 N3 123.7(3) . . ?
O6 C8 N3 109.0(2) . . ?
O6 C9 H9A 109.5 . . ?
O6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 O1 125.4(3) . . ?
O2 C10 C11 119.6(2) . . ?
O1 C10 C11 115.0(2) . . ?
C12 C11 C16 119.6(2) . . ?
C12 C11 C10 119.9(3) . . ?
C16 C11 C10 120.5(2) . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
O3 C13 C14 121.5(2) . . ?
O3 C13 C12 117.6(3) . . ?
C14 C13 C12 120.9(3) . . ?
O4 C14 C13 117.7(3) . . ?
O4 C14 C15 123.1(3) . . ?
C13 C14 C15 119.2(2) . . ?
O5 C15 C16 124.2(3) . . ?
O5 C15 C14 115.7(2) . . ?
C16 C15 C14 120.1(3) . . ?
C15 C16 C11 120.3(3) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C5 N1 C1 118.9(3) . . ?
C5 N1 Cu1 115.3(2) . . ?
C1 N1 Cu1 125.7(2) . . ?
C7 N2 C6 117.2(2) . . ?
C7 N2 Cu1 127.6(2) . . ?
C6 N2 Cu1 115.24(18) . . ?
C8 N3 C7 128.4(2) . . ?
C8 N3 H3B 115.8 . . ?
C7 N3 H3B 115.8 . . ?
C8 N4 Cu1 127.6(2) . . ?
C8 N4 H4B 116.2 . . ?
Cu1 N4 H4B 116.2 . . ?
C7 N5 H5A 120.0 . . ?
C7 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C10 O1 Cu1 133.27(19) . . ?
C13 O3 H3A 109.5 . . ?
C14 O4 H4A 109.5 . . ?
C15 O5 H5 109.5 . . ?
C8 O6 C9 118.5(2) . . ?
H7B O7 H7A 104.44(15) . . ?
H8B O8 H8A 104.47(16) . . ?
H10B O9 H10A 104.47(15) . . ?
N4 Cu1 O1 95.33(9) . . ?
N4 Cu1 N2 91.18(10) . . ?
O1 Cu1 N2 172.98(9) . . ?
N4 Cu1 N1 174.04(9) . . ?
O1 Cu1 N1 90.62(9) . . ?
N2 Cu1 N1 82.89(10) . . ?
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
C1 N1 1.351(4) . ?
C1 C2 1.362(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 N1 1.335(4) . ?
C5 C6 1.497(4) . ?
C6 N2 1.451(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.296(4) . ?
C7 N5 1.337(4) . ?
C7 N3 1.373(4) . ?
C8 N4 1.270(3) . ?
C8 O6 1.327(3) . ?
C8 N3 1.358(4) . ?
C9 O6 1.439(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O2 1.240(3) . ?
C10 O1 1.270(3) . ?
C10 C11 1.512(4) . ?
C11 C12 1.382(4) . ?
C11 C16 1.391(4) . ?
C12 C13 1.383(4) . ?
C12 H12 0.9300 . ?
C13 O3 1.365(3) . ?
C13 C14 1.380(4) . ?
C14 O4 1.366(3) . ?
C14 C15 1.391(4) . ?
C15 O5 1.372(3) . ?
C15 C16 1.379(4) . ?
C16 H16 0.9300 . ?
N1 Cu1 1.973(2) . ?
N2 Cu1 1.947(2) . ?
N3 H3B 0.8600 . ?
N4 Cu1 1.920(2) . ?
N4 H4B 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
O1 Cu1 1.9310(19) . ?
O3 H3A 0.73(4) . ?
O4 H4A 0.72(4) . ?
O5 H5 0.84(4) . ?
O7 H7B 0.9584(11) . ?
O7 H7A 0.9584(11) . ?
O8 H8B 0.9582(11) . ?
O8 H8A 0.9582(11) . ?
O9 H10B 0.9582(11) . ?
O9 H10A 0.9582(11) . ?
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
N1 C1 C2 C3 0.0(6) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C3 C4 C5 N1 0.9(5) . . . . ?
C3 C4 C5 C6 -179.5(3) . . . . ?
N1 C5 C6 N2 1.2(4) . . . . ?
C4 C5 C6 N2 -178.4(3) . . . . ?
O2 C10 C11 C12 2.4(4) . . . . ?
O1 C10 C11 C12 -175.9(3) . . . . ?
O2 C10 C11 C16 -179.9(3) . . . . ?
O1 C10 C11 C16 1.9(4) . . . . ?
C16 C11 C12 C13 -1.8(4) . . . . ?
C10 C11 C12 C13 176.0(3) . . . . ?
C11 C12 C13 O3 -178.9(3) . . . . ?
C11 C12 C13 C14 1.8(4) . . . . ?
O3 C13 C14 O4 1.1(4) . . . . ?
C12 C13 C14 O4 -179.6(3) . . . . ?
O3 C13 C14 C15 -179.3(3) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
O4 C14 C15 O5 -2.4(4) . . . . ?
C13 C14 C15 O5 178.1(3) . . . . ?
O4 C14 C15 C16 177.9(3) . . . . ?
C13 C14 C15 C16 -1.7(4) . . . . ?
O5 C15 C16 C11 -178.1(3) . . . . ?
C14 C15 C16 C11 1.6(4) . . . . ?
C12 C11 C16 C15 0.1(4) . . . . ?
C10 C11 C16 C15 -177.7(3) . . . . ?
C4 C5 N1 C1 -0.6(5) . . . . ?
C6 C5 N1 C1 179.8(3) . . . . ?
C4 C5 N1 Cu1 178.1(3) . . . . ?
C6 C5 N1 Cu1 -1.5(3) . . . . ?
C2 C1 N1 C5 0.1(5) . . . . ?
C2 C1 N1 Cu1 -178.4(3) . . . . ?
N5 C7 N2 C6 -0.2(4) . . . . ?
N3 C7 N2 C6 -179.3(3) . . . . ?
N5 C7 N2 Cu1 -178.3(2) . . . . ?
N3 C7 N2 Cu1 2.5(4) . . . . ?
C5 C6 N2 C7 -178.6(3) . . . . ?
C5 C6 N2 Cu1 -0.2(3) . . . . ?
N4 C8 N3 C7 -2.9(5) . . . . ?
O6 C8 N3 C7 177.3(3) . . . . ?
N2 C7 N3 C8 0.6(5) . . . . ?
N5 C7 N3 C8 -178.6(3) . . . . ?
O6 C8 N4 Cu1 -178.5(2) . . . . ?
N3 C8 N4 Cu1 1.8(5) . . . . ?
O2 C10 O1 Cu1 -0.2(5) . . . . ?
C11 C10 O1 Cu1 177.89(18) . . . . ?
N4 C8 O6 C9 -2.1(5) . . . . ?
N3 C8 O6 C9 177.7(3) . . . . ?
