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#$Date: 2021-07-07 11:16:08 +0300 (Wed, 07 Jul 2021) $
#$Revision: 267322 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/39/1563997.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_1563997
loop_
_publ_author_name
'Gomathi, V.'
'Selvameena, R.'
_publ_section_title
;
 Spectroscopic investigation, fluorescence quenching, in vitro
 antibacterial and cytotoxicity assay of Co(II) and Ni(II) complexes
 containing 4-((3-ethoxy-2-hydroxy
 benzylidene)amino)-N-(pyridin-2-yl)benzenesulfonamide
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              42
_journal_page_last               46
_journal_paper_doi               10.1016/j.ica.2018.05.007
_journal_volume                  480
_journal_year                    2018
_chemical_formula_sum            'C20 H19 N3 O4 S'
_chemical_formula_weight         397.44
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.661(2)
_cell_angle_beta                 99.537(2)
_cell_angle_gamma                111.426(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0754(3)
_cell_length_b                   8.3500(3)
_cell_length_c                   15.2691(5)
_cell_measurement_reflns_used    9259
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.4
_cell_measurement_theta_min      2.63
_cell_volume                     938.75(6)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16718
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.9532
_exptl_absorpt_correction_T_min  0.9236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0449P)²+0.2932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0985
_reflns_number_gt                2833
_reflns_number_total             3286
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2018-480-42.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1563997
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0897(2) 0.6594(2) 0.89337(10) 0.0407(4) Uani 1 1 d . . .
C2 C 1.1531(2) 0.7644(2) 0.82740(12) 0.0513(4) Uani 1 1 d . . .
H2 H 1.0711 0.7823 0.7823 0.062 Uiso 1 1 calc R . .
C3 C 1.3344(3) 0.8402(2) 0.82925(14) 0.0602(5) Uani 1 1 d . . .
H3 H 1.3750 0.9082 0.7848 0.072 Uiso 1 1 calc R . .
C4 C 1.4593(3) 0.8176(3) 0.89636(15) 0.0659(5) Uani 1 1 d . . .
H4 H 1.5830 0.8685 0.8971 0.079 Uiso 1 1 calc R . .
C5 C 1.3968(2) 0.7198(3) 0.96069(14) 0.0588(5) Uani 1 1 d . . .
H5 H 1.4784 0.7046 1.0070 0.071 Uiso 1 1 calc R . .
C6 C 0.7435(2) 0.4095(2) 0.73823(10) 0.0451(4) Uani 1 1 d . . .
C7 C 0.6792(3) 0.2349(3) 0.74334(13) 0.0667(6) Uani 1 1 d . . .
H7 H 0.6318 0.1919 0.7927 0.080 Uiso 1 1 calc R . .
C8 C 0.6841(3) 0.1222(3) 0.67581(14) 0.0720(6) Uani 1 1 d . . .
H8 H 0.6400 0.0038 0.6800 0.086 Uiso 1 1 calc R . .
C9 C 0.7541(2) 0.1841(2) 0.60178(11) 0.0486(4) Uani 1 1 d . . .
C10 C 0.8166(3) 0.3592(3) 0.59734(12) 0.0598(5) Uani 1 1 d . . .
H10 H 0.8632 0.4025 0.5478 0.072 Uiso 1 1 calc R . .
C11 C 0.8120(3) 0.4728(3) 0.66489(12) 0.0595(5) Uani 1 1 d . . .
H11 H 0.8550 0.5912 0.6607 0.071 Uiso 1 1 calc R . .
C12 C 0.7327(3) -0.0789(3) 0.52865(12) 0.0562(5) Uani 1 1 d . . .
H12 H 0.7049 -0.1299 0.5799 0.067 Uiso 1 1 calc R . .
C13 C 0.7391(2) -0.1853(2) 0.45271(11) 0.0511(4) Uani 1 1 d . . .
C14 C 0.6919(3) -0.3629(3) 0.45589(15) 0.0688(6) Uani 1 1 d . . .
H14 H 0.6599 -0.4109 0.5073 0.083 Uiso 1 1 calc R . .
C15 C 0.6921(3) -0.4668(3) 0.38446(16) 0.0725(6) Uani 1 1 d . . .
H15 H 0.6582 -0.5853 0.3870 0.087 Uiso 1 1 calc R . .
C16 C 0.7425(3) -0.3966(2) 0.30816(13) 0.0583(5) Uani 1 1 d . . .
H16 H 0.7424 -0.4684 0.2597 0.070 Uiso 1 1 calc R . .
C17 C 0.7927(2) -0.2220(2) 0.30324(11) 0.0481(4) Uani 1 1 d . . .
C18 C 0.7898(2) -0.1142(2) 0.37594(11) 0.0459(4) Uani 1 1 d . . .
C19 C 0.8624(3) -0.2431(2) 0.15856(13) 0.0608(5) Uani 1 1 d . . .
H19A H 0.7453 -0.3321 0.1322 0.073 Uiso 1 1 calc R . .
H19B H 0.9457 -0.2990 0.1791 0.073 Uiso 1 1 calc R . .
C20 C 0.9319(4) -0.1259(3) 0.09158(16) 0.0937(8) Uani 1 1 d . . .
H20A H 0.9441 -0.1916 0.0415 0.141 Uiso 1 1 calc R . .
H20B H 1.0481 -0.0389 0.1182 0.141 Uiso 1 1 calc R . .
H20C H 0.8486 -0.0713 0.0717 0.141 Uiso 1 1 calc R . .
N1 N 1.21744(18) 0.64414(17) 0.95836(9) 0.0452(3) Uani 1 1 d . . .
H1 H 1.1821 0.5828 1.0004 0.054 Uiso 1 1 calc R . .
N2 N 0.91763(18) 0.56889(18) 0.90240(9) 0.0465(3) Uani 1 1 d . . .
N3 N 0.7636(2) 0.0811(2) 0.52796(9) 0.0529(4) Uani 1 1 d . . .
O1 O 0.59304(16) 0.46354(18) 0.86802(8) 0.0616(4) Uani 1 1 d . . .
O2 O 0.75599(18) 0.71196(17) 0.79386(9) 0.0632(4) Uani 1 1 d . . .
O3 O 0.8364(2) 0.05581(15) 0.36836(8) 0.0634(4) Uani 1 1 d . . .
H3A H 0.8295 0.1054 0.4145 0.095 Uiso 1 1 calc R . .
O4 O 0.84572(19) -0.14031(16) 0.23197(8) 0.0615(4) Uani 1 1 d . . .
S1 S 0.74523(6) 0.55223(6) 0.82801(3) 0.04896(15) 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'
S S 0.1246 0.1234 '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
N2 C1 N1 113.82(14) . .
N2 C1 C2 129.69(16) . .
N1 C1 C2 116.49(15) . .
C3 C2 C1 120.13(17) . .
C3 C2 H2 119.9 . .
C1 C2 H2 119.9 . .
C2 C3 C4 121.01(18) . .
C2 C3 H3 119.5 . .
C4 C3 H3 119.5 . .
C5 C4 C3 118.29(18) . .
C5 C4 H4 120.9 . .
C3 C4 H4 120.9 . .
N1 C5 C4 120.56(18) . .
N1 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C7 C6 C11 119.73(16) . .
C7 C6 S1 119.66(13) . .
C11 C6 S1 120.58(14) . .
C6 C7 C8 120.51(17) . .
C6 C7 H7 119.7 . .
C8 C7 H7 119.7 . .
C7 C8 C9 120.46(19) . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
C10 C9 C8 118.32(17) . .
C10 C9 N3 116.19(15) . .
C8 C9 N3 125.48(17) . .
C9 C10 C11 121.46(17) . .
C9 C10 H10 119.3 . .
C11 C10 H10 119.3 . .
C6 C11 C10 119.52(18) . .
C6 C11 H11 120.2 . .
C10 C11 H11 120.2 . .
N3 C12 C13 122.57(17) . .
N3 C12 H12 118.7 . .
C13 C12 H12 118.7 . .
C18 C13 C14 119.22(17) . .
C18 C13 C12 121.27(17) . .
C14 C13 C12 119.51(17) . .
C15 C14 C13 120.72(19) . .
C15 C14 H14 119.6 . .
C13 C14 H14 119.6 . .
C14 C15 C16 120.18(19) . .
C14 C15 H15 119.9 . .
C16 C15 H15 119.9 . .
C17 C16 C15 120.66(18) . .
C17 C16 H16 119.7 . .
C15 C16 H16 119.7 . .
O4 C17 C16 125.23(16) . .
O4 C17 C18 115.21(15) . .
C16 C17 C18 119.55(17) . .
O3 C18 C13 122.26(15) . .
O3 C18 C17 118.10(15) . .
C13 C18 C17 119.64(16) . .
O4 C19 C20 107.71(16) . .
O4 C19 H19A 110.2 . .
C20 C19 H19A 110.2 . .
O4 C19 H19B 110.2 . .
C20 C19 H19B 110.2 . .
H19A C19 H19B 108.5 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C5 N1 C1 123.47(15) . .
C5 N1 H1 118.3 . .
C1 N1 H1 118.3 . .
C1 N2 S1 122.36(12) . .
C12 N3 C9 122.42(16) . .
C18 O3 H3A 109.5 . .
C17 O4 C19 117.17(14) . .
O2 S1 O1 117.89(8) . .
O2 S1 N2 113.94(8) . .
O1 S1 N2 103.99(8) . .
O2 S1 C6 107.37(8) . .
O1 S1 C6 107.61(8) . .
N2 S1 C6 105.23(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.352(2) .
C1 N1 1.354(2) .
C1 C2 1.404(2) .
C2 C3 1.361(3) .
C2 H2 0.9300 .
C3 C4 1.384(3) .
C3 H3 0.9300 .
C4 C5 1.351(3) .
C4 H4 0.9300 .
C5 N1 1.345(2) .
C5 H5 0.9300 .
C6 C7 1.368(3) .
C6 C11 1.373(2) .
C6 S1 1.7692(17) .
C7 C8 1.379(3) .
C7 H7 0.9300 .
C8 C9 1.385(3) .
C8 H8 0.9300 .
C9 C10 1.370(3) .
C9 N3 1.416(2) .
C10 C11 1.383(3) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 N3 1.267(2) .
C12 C13 1.447(3) .
C12 H12 0.9300 .
C13 C18 1.393(2) .
C13 C14 1.395(3) .
C14 C15 1.363(3) .
C14 H14 0.9300 .
C15 C16 1.383(3) .
C15 H15 0.9300 .
C16 C17 1.373(3) .
C16 H16 0.9300 .
C17 O4 1.358(2) .
C17 C18 1.405(2) .
C18 O3 1.345(2) .
C19 O4 1.434(2) .
C19 C20 1.484(3) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
N1 H1 0.8600 .
N2 S1 1.6024(14) .
O1 S1 1.4345(13) .
O2 S1 1.4329(14) .
O3 H3A 0.8200 .
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
C2 H2 O2 0.93 2.43 3.024(2) 121.5 .
C5 H5 O1 0.93 2.44 3.096(2) 127.2 2_767
C19 H19A O1 0.97 2.54 3.402(2) 147.3 2_656
N1 H1 N2 0.86 2.07 2.928(2) 176.8 2_767
N1 H1 O1 0.86 2.62 3.1719(19) 123.1 2_767
N1 H1 S1 0.86 2.95 3.7352(15) 151.8 2_767
O3 H3A N3 0.82 1.89 2.6164(18) 146.4 .
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
N2 C1 C2 C3 -177.75(16) . . . .
N1 C1 C2 C3 2.1(2) . . . .
C1 C2 C3 C4 -0.9(3) . . . .
C2 C3 C4 C5 -0.7(3) . . . .
C3 C4 C5 N1 1.1(3) . . . .
C11 C6 C7 C8 0.6(3) . . . .
S1 C6 C7 C8 -177.16(17) . . . .
C6 C7 C8 C9 0.0(4) . . . .
C7 C8 C9 C10 -0.5(3) . . . .
C7 C8 C9 N3 -178.98(19) . . . .
C8 C9 C10 C11 0.5(3) . . . .
N3 C9 C10 C11 179.11(17) . . . .
C7 C6 C11 C10 -0.6(3) . . . .
S1 C6 C11 C10 177.14(15) . . . .
C9 C10 C11 C6 0.1(3) . . . .
N3 C12 C13 C18 3.5(3) . . . .
N3 C12 C13 C14 -175.73(18) . . . .
C18 C13 C14 C15 -1.1(3) . . . .
C12 C13 C14 C15 178.24(19) . . . .
C13 C14 C15 C16 1.1(3) . . . .
C14 C15 C16 C17 -0.1(3) . . . .
C15 C16 C17 O4 179.41(18) . . . .
C15 C16 C17 C18 -1.1(3) . . . .
C14 C13 C18 O3 179.80(17) . . . .
C12 C13 C18 O3 0.5(3) . . . .
C14 C13 C18 C17 -0.1(3) . . . .
C12 C13 C18 C17 -179.38(15) . . . .
O4 C17 C18 O3 0.8(2) . . . .
C16 C17 C18 O3 -178.75(16) . . . .
O4 C17 C18 C13 -179.29(15) . . . .
C16 C17 C18 C13 1.1(3) . . . .
C4 C5 N1 C1 0.1(3) . . . .
N2 C1 N1 C5 178.16(15) . . . .
C2 C1 N1 C5 -1.7(2) . . . .
N1 C1 N2 S1 -173.55(11) . . . .
C2 C1 N2 S1 6.3(2) . . . .
C13 C12 N3 C9 178.87(16) . . . .
C10 C9 N3 C12 170.58(17) . . . .
C8 C9 N3 C12 -10.9(3) . . . .
C16 C17 O4 C19 -4.5(3) . . . .
C18 C17 O4 C19 175.96(15) . . . .
C20 C19 O4 C17 -176.65(18) . . . .
C1 N2 S1 O2 -44.33(15) . . . .
C1 N2 S1 O1 -173.97(13) . . . .
C1 N2 S1 C6 73.01(14) . . . .
C7 C6 S1 O2 -159.93(15) . . . .
C11 C6 S1 O2 22.35(17) . . . .
C7 C6 S1 O1 -32.09(17) . . . .
C11 C6 S1 O1 150.19(15) . . . .
C7 C6 S1 N2 78.35(16) . . . .
C11 C6 S1 N2 -99.37(16) . . . .
