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#$Date: 2019-11-10 19:45:05 +0200 (Sun, 10 Nov 2019) $
#$Revision: 226078 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/60/4516053.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_4516053
loop_
_publ_author_name
'Santos, Ane F.'
'Ferreira, Isabella P.'
'Pinheiro, Carlos B.'
'Santos, Verlane G.'
'Lopes, Miriam T. P.'
'Teixeira, Letícia R'
'Rocha, Willian R.'
'Rodrigues, Gabriel L. S.'
'Beraldo, Heloisa'
_publ_section_title
;
 [Ag(L)NO₃] Complexes with 2-Benzoylpyridine-Derived
 Hydrazones: Cytotoxic Activity and Interaction with Biomolecules.
;
_journal_issue                   6
_journal_name_full               'ACS omega'
_journal_page_first              7027
_journal_page_last               7035
_journal_paper_doi               10.1021/acsomega.8b00533
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C20 H17 Ag N4 O4'
_chemical_formula_sum            'C20 H17 Ag N4 O4'
_chemical_formula_weight         485.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2018-02-14 deposited with the CCDC.
2018-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.044(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.3045(5)
_cell_length_b                   14.5456(7)
_cell_length_c                   21.5645(8)
_cell_measurement_reflns_used    5007
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.9160
_cell_measurement_theta_min      2.7360
_cell_volume                     3830.4(3)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14044
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         1.693
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.088
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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            colourless
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_description       prism
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0337
_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)+(0.0225P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0648
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3089
_reflns_number_total             3925
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao8b00533_si_003.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               4516053
_shelx_shelxl_version_number     2017/1
_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   0.909
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
C2 C 0.8398(2) 0.3202(2) -0.12311(12) 0.0125(6) Uani 1 1 d . .
C3 C 0.8519(2) 0.2890(2) -0.18259(13) 0.0181(7) Uani 1 1 d . .
H3 H 0.857621 0.331274 -0.215587 0.022 Uiso 1 1 calc R U
C4 C 0.8554(2) 0.1952(2) -0.19323(14) 0.0238(7) Uani 1 1 d . .
H4 H 0.864035 0.172124 -0.233550 0.029 Uiso 1 1 calc R U
C5 C 0.8461(3) 0.1359(2) -0.14432(15) 0.0269(8) Uani 1 1 d . .
H5 H 0.846736 0.071218 -0.150539 0.032 Uiso 1 1 calc R U
C6 C 0.8360(2) 0.1721(2) -0.08605(15) 0.0241(7) Uani 1 1 d . .
H6 H 0.830958 0.130822 -0.052380 0.029 Uiso 1 1 calc R U
C7 C 0.8369(2) 0.4200(2) -0.10985(12) 0.0124(6) Uani 1 1 d . .
C8 C 0.8841(2) 0.5588(2) 0.02526(13) 0.0127(6) Uani 1 1 d . .
C9 C 0.8842(2) 0.6600(2) 0.03640(12) 0.0139(6) Uani 1 1 d . .
C10 C 0.8776(2) 0.6892(2) 0.09729(13) 0.0182(7) Uani 1 1 d . .
H10 H 0.874404 0.645290 0.129637 0.022 Uiso 1 1 calc R U
C11 C 0.8757(2) 0.7823(2) 0.11072(15) 0.0245(8) Uani 1 1 d . .
H11 H 0.870626 0.801463 0.152389 0.029 Uiso 1 1 calc R U
C12 C 0.8811(2) 0.8485(2) 0.06457(15) 0.0248(8) Uani 1 1 d . .
C13 C 0.8897(2) 0.8186(2) 0.00412(15) 0.0222(7) Uani 1 1 d . .
H13 H 0.894810 0.862535 -0.027975 0.027 Uiso 1 1 calc R U
C14 C 0.8910(2) 0.7258(2) -0.01004(13) 0.0175(7) Uani 1 1 d . .
H14 H 0.896656 0.706849 -0.051677 0.021 Uiso 1 1 calc R U
C15 C 0.8058(2) 0.4872(2) -0.16121(12) 0.0125(6) Uani 1 1 d . .
C16 C 0.7002(2) 0.4839(2) -0.19324(12) 0.0146(6) Uani 1 1 d . .
H16 H 0.650963 0.436855 -0.184262 0.018 Uiso 1 1 calc R U
C17 C 0.6674(2) 0.5498(2) -0.23826(12) 0.0189(7) Uani 1 1 d . .
H17 H 0.595370 0.548061 -0.259944 0.023 Uiso 1 1 calc R U
C18 C 0.7393(2) 0.6180(2) -0.25158(13) 0.0217(7) Uani 1 1 d . .
H18 H 0.716504 0.663014 -0.282360 0.026 Uiso 1 1 calc R U
C19 C 0.8446(3) 0.6208(2) -0.22017(13) 0.0228(7) Uani 1 1 d . .
H19 H 0.893743 0.667695 -0.229609 0.027 Uiso 1 1 calc R U
C20 C 0.8782(2) 0.5557(2) -0.17513(13) 0.0187(7) Uani 1 1 d . .
H20 H 0.950476 0.557598 -0.153766 0.022 Uiso 1 1 calc R U
C21 C 0.8768(3) 0.9495(2) 0.07912(18) 0.0431(10) Uani 1 1 d . .
H21A H 0.801037 0.971241 0.070831 0.065 Uiso 1 1 calc R U
H21B H 0.922556 0.983427 0.052793 0.065 Uiso 1 1 calc R U
H21C H 0.904106 0.959714 0.123213 0.065 Uiso 1 1 calc R U
N1 N 0.83297(19) 0.26215(17) -0.07480(10) 0.0168(5) Uani 1 1 d . .
N2 N 0.86152(17) 0.44295(17) -0.05172(10) 0.0125(5) Uani 1 1 d . .
N3 N 0.85999(17) 0.53384(17) -0.03665(10) 0.0129(5) Uani 1 1 d . .
H3N H 0.843957 0.575749 -0.065766 0.015 Uiso 1 1 calc R U
N4 N 0.94041(19) 0.21490(19) 0.13722(11) 0.0207(6) Uani 1 1 d . .
O1 O 0.90075(15) 0.50177(13) 0.06679(8) 0.0159(5) Uani 1 1 d . .
O2 O 0.92260(16) 0.30126(15) 0.13004(9) 0.0213(5) Uani 1 1 d . .
O3 O 0.9271(2) 0.16474(16) 0.09053(11) 0.0352(6) Uani 1 1 d . .
O4 O 0.9702(2) 0.18509(18) 0.19025(11) 0.0416(7) Uani 1 1 d . .
Ag1 Ag 0.86868(2) 0.32618(2) 0.02650(2) 0.01851(8) 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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5 1 1 0.0406 -5.0002 1.0001 0.9999 0.2366 -0.1190 0.1236
0 -5 4 0.0196 -0.0000 -5.0006 4.0004 -0.0524 0.1957 0.1897
0 5 -4 0.0196 0.0000 5.0006 -4.0004 0.0524 -0.1957 -0.1897
0 4 5 0.0127 0.0001 4.0004 5.0006 -0.1077 -0.2230 0.0651
0 -4 -5 0.0127 -0.0001 -4.0004 -5.0006 0.1077 0.2230 -0.0651
5 -1 -1 0.0406 5.0002 -1.0001 -0.9999 -0.2366 0.1190 -0.1236
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_3
N1 C2 C3 122.2(3) .
N1 C2 C7 117.3(2) .
C3 C2 C7 120.5(3) .
C4 C3 C2 119.0(3) .
C4 C3 H3 120.5 .
C2 C3 H3 120.5 .
C5 C4 C3 118.9(3) .
C5 C4 H4 120.6 .
C3 C4 H4 120.6 .
C4 C5 C6 118.8(3) .
C4 C5 H5 120.6 .
C6 C5 H5 120.6 .
N1 C6 C5 123.2(3) .
N1 C6 H6 118.4 .
C5 C6 H6 118.4 .
N2 C7 C2 115.5(2) .
N2 C7 C15 123.9(3) .
C2 C7 C15 120.6(2) .
O1 C8 N3 121.9(3) .
O1 C8 C9 123.8(2) .
N3 C8 C9 114.3(2) .
C10 C9 C14 118.9(3) .
C10 C9 C8 117.0(3) .
C14 C9 C8 124.1(2) .
C11 C10 C9 120.0(3) .
C11 C10 H10 120.0 .
C9 C10 H10 120.0 .
C10 C11 C12 121.5(3) .
C10 C11 H11 119.2 .
C12 C11 H11 119.2 .
C13 C12 C11 118.0(3) .
C13 C12 C21 120.6(3) .
C11 C12 C21 121.3(3) .
C14 C13 C12 121.1(3) .
C14 C13 H13 119.5 .
C12 C13 H13 119.5 .
C13 C14 C9 120.5(3) .
C13 C14 H14 119.8 .
C9 C14 H14 119.8 .
C20 C15 C16 119.9(3) .
C20 C15 C7 121.0(2) .
C16 C15 C7 119.0(3) .
C17 C16 C15 119.8(3) .
C17 C16 H16 120.1 .
C15 C16 H16 120.1 .
C18 C17 C16 120.1(3) .
C18 C17 H17 120.0 .
C16 C17 H17 120.0 .
C17 C18 C19 120.2(3) .
C17 C18 H18 119.9 .
C19 C18 H18 119.9 .
C20 C19 C18 120.2(3) .
C20 C19 H19 119.9 .
C18 C19 H19 119.9 .
C19 C20 C15 119.8(3) .
C19 C20 H20 120.1 .
C15 C20 H20 120.1 .
C12 C21 H21A 109.5 .
C12 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C12 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
C6 N1 C2 117.9(2) .
C6 N1 Ag1 123.3(2) .
C2 N1 Ag1 116.35(19) .
C7 N2 N3 118.2(2) .
C7 N2 Ag1 118.96(19) .
N3 N2 Ag1 121.48(16) .
N2 N3 C8 118.6(2) .
N2 N3 H3N 120.7 .
C8 N3 H3N 120.7 .
O4 N4 O3 122.7(3) .
O4 N4 O2 118.9(3) .
O3 N4 O2 118.4(2) .
C8 O1 Ag1 113.64(17) .
N4 O2 Ag1 107.41(16) .
N4 O3 Ag1 84.62(17) .
O2 Ag1 N1 147.22(8) .
O2 Ag1 N2 141.85(8) .
N1 Ag1 N2 68.97(8) .
O2 Ag1 O1 79.77(7) .
N1 Ag1 O1 132.07(7) .
N2 Ag1 O1 63.10(7) .
O2 Ag1 O3 49.54(7) .
N1 Ag1 O3 97.69(8) .
N2 Ag1 O3 159.83(7) .
O1 Ag1 O3 128.27(6) .
O2 Ag1 Ag1 121.71(5) 2_655
N1 Ag1 Ag1 65.59(6) 2_655
N2 Ag1 Ag1 77.36(5) 2_655
O1 Ag1 Ag1 102.62(4) 2_655
O3 Ag1 Ag1 111.73(5) 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 N1 1.352(3) .
C2 C3 1.386(4) .
C2 C7 1.481(4) .
C3 C4 1.385(4) .
C3 H3 0.9500 .
C4 C5 1.378(4) .
C4 H4 0.9500 .
C5 C6 1.382(4) .
C5 H5 0.9500 .
C6 N1 1.334(4) .
C6 H6 0.9500 .
C7 N2 1.297(3) .
C7 C15 1.491(4) .
C8 O1 1.220(3) .
C8 N3 1.380(3) .
C8 C9 1.490(4) .
C9 C10 1.392(4) .
C9 C14 1.396(4) .
C10 C11 1.387(4) .
C10 H10 0.9500 .
C11 C12 1.392(5) .
C11 H11 0.9500 .
C12 C13 1.391(4) .
C12 C21 1.505(5) .
C13 C14 1.384(4) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 C20 1.393(4) .
C15 C16 1.396(4) .
C16 C17 1.389(4) .
C16 H16 0.9500 .
C17 C18 1.382(4) .
C17 H17 0.9500 .
C18 C19 1.387(4) .
C18 H18 0.9500 .
C19 C20 1.384(4) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
N1 Ag1 2.366(2) .
N2 N3 1.362(3) .
N2 Ag1 2.388(2) .
N3 H3N 0.8800 .
N4 O4 1.236(3) .
N4 O3 1.238(3) .
N4 O2 1.281(3) .
O1 Ag1 2.7110(19) .
O2 Ag1 2.2789(19) .
O3 Ag1 2.774(2) .
Ag1 Ag1 3.0028(5) 2_655
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
N1 C2 C3 C4 1.0(4)
C7 C2 C3 C4 179.3(2)
C2 C3 C4 C5 0.4(4)
C3 C4 C5 C6 -1.4(5)
C4 C5 C6 N1 1.1(5)
N1 C2 C7 N2 20.2(3)
C3 C2 C7 N2 -158.2(2)
N1 C2 C7 C15 -158.9(2)
C3 C2 C7 C15 22.7(4)
O1 C8 C9 C10 -15.3(4)
N3 C8 C9 C10 162.7(2)
O1 C8 C9 C14 164.3(3)
N3 C8 C9 C14 -17.7(4)
C14 C9 C10 C11 1.3(4)
C8 C9 C10 C11 -179.1(2)
C9 C10 C11 C12 -0.5(4)
C10 C11 C12 C13 -0.7(5)
C10 C11 C12 C21 178.8(3)
C11 C12 C13 C14 1.1(5)
C21 C12 C13 C14 -178.4(3)
C12 C13 C14 C9 -0.3(4)
C10 C9 C14 C13 -0.9(4)
C8 C9 C14 C13 179.5(3)
N2 C7 C15 C20 61.2(4)
C2 C7 C15 C20 -119.8(3)
N2 C7 C15 C16 -115.2(3)
C2 C7 C15 C16 63.8(3)
C20 C15 C16 C17 -0.8(4)
C7 C15 C16 C17 175.6(2)
C15 C16 C17 C18 0.4(4)
C16 C17 C18 C19 0.1(4)
C17 C18 C19 C20 -0.2(5)
C18 C19 C20 C15 -0.2(4)
C16 C15 C20 C19 0.7(4)
C7 C15 C20 C19 -175.6(3)
C5 C6 N1 C2 0.3(4)
C5 C6 N1 Ag1 -161.1(2)
C3 C2 N1 C6 -1.3(4)
C7 C2 N1 C6 -179.7(2)
C3 C2 N1 Ag1 161.3(2)
C7 C2 N1 Ag1 -17.0(3)
C2 C7 N2 N3 -179.8(2)
C15 C7 N2 N3 -0.7(4)
C2 C7 N2 Ag1 -13.1(3)
C15 C7 N2 Ag1 165.97(19)
C7 N2 N3 C8 178.9(2)
Ag1 N2 N3 C8 12.5(3)
O1 C8 N3 N2 -4.0(4)
C9 C8 N3 N2 177.9(2)
N3 C8 O1 Ag1 -4.9(3)
C9 C8 O1 Ag1 173.01(18)
O4 N4 O2 Ag1 -179.6(2)
O3 N4 O2 Ag1 0.5(3)
O4 N4 O3 Ag1 179.7(3)
O2 N4 O3 Ag1 -0.4(2)
