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#$Date: 2022-01-06 10:15:08 +0200 (Thu, 06 Jan 2022) $
#$Revision: 271824 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/59/1565920.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_1565920
loop_
_publ_author_name
'Debnath, Paresh'
'Das, Ankit'
'Singh, Keisham Surjit'
'Yama, Tage'
'Singh, S.Sureshkumar'
'Butcher, Ray J.'
'Sieroń, Lesław'
'Maniukiewicz, Waldemar'
_publ_section_title
;
 Synthesis, structural characterization and antimicrobial activities of
 triorganotin(IV)azo-carboxylates derived from ortho/para-amino benzoic
 acids and β-naphthol
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119172
_journal_paper_doi               10.1016/j.ica.2019.119172
_journal_volume                  498
_journal_year                    2019
_chemical_formula_moiety         'C20 H20 N2 O3 Sn'
_chemical_formula_sum            'C20 H20 N2 O3 Sn'
_chemical_formula_weight         455.07
_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   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 100.191(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2778(6)
_cell_length_b                   9.6780(4)
_cell_length_c                   30.1272(13)
_cell_measurement_reflns_used    7116
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.50
_cell_measurement_theta_min      2.61
_cell_volume                     3810.3(3)
_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_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0814
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            31349
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.619
_exptl_absorpt_coefficient_mu    1.362
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker. 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_description       plate
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         2.427
_refine_diff_density_min         -0.982
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       0.00024(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0665
_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)+(0.0373P)²+70.3615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1547
_refine_ls_wR_factor_ref         0.1669
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2510
_reflns_number_total             3360
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2019-498-119172.cif
_cod_data_source_block           kss6
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1565920
_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   0.876
_shelx_estimated_absorpt_t_max   0.935
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
C1 C 0.7730(7) 0.0847(10) 0.6792(3) 0.043(2) Uani 1 1 d . . . . .
C2 C 0.8005(8) 0.1319(9) 0.6360(3) 0.044(2) Uani 1 1 d . . . . .
C3 C 0.8495(8) 0.0431(10) 0.6107(3) 0.050(2) Uani 1 1 d . . . . .
H13 H 0.863841 -0.046607 0.620984 0.060 Uiso 1 1 calc R U . . .
C4 C 0.8777(8) 0.0840(10) 0.5706(3) 0.054(3) Uani 1 1 d . . . . .
H14 H 0.912233 0.023690 0.554479 0.064 Uiso 1 1 calc R U . . .
C5 C 0.8533(8) 0.2173(10) 0.5549(3) 0.046(2) Uani 1 1 d . . . . .
C6 C 0.8056(8) 0.3083(11) 0.5796(3) 0.054(3) Uani 1 1 d . . . . .
H15 H 0.792314 0.398403 0.569489 0.065 Uiso 1 1 calc R U . . .
C7 C 0.7774(8) 0.2651(10) 0.6193(3) 0.050(3) Uani 1 1 d . . . . .
H16 H 0.742467 0.325585 0.635216 0.060 Uiso 1 1 calc R U . . .
C8 C 0.9084(8) 0.4081(11) 0.4613(3) 0.052(3) Uani 1 1 d . . . . .
C9 C 0.9623(9) 0.3090(13) 0.4369(4) 0.061(3) Uani 1 1 d . . . . .
C10 C 0.9998(9) 0.3568(13) 0.3979(4) 0.065(3) Uani 1 1 d . . . . .
H12 H 1.036689 0.296869 0.382694 0.078 Uiso 1 1 calc R U . . .
C11 C 0.9826(9) 0.4862(14) 0.3830(4) 0.070(3) Uani 1 1 d . . . . .
H11 H 1.008005 0.512341 0.357373 0.084 Uiso 1 1 calc R U . . .
C12 C 0.9282(8) 0.5863(13) 0.4038(3) 0.058(3) Uani 1 1 d . . . . .
C13 C 0.8915(8) 0.5493(11) 0.4437(3) 0.052(3) Uani 1 1 d . . . . .
C14 C 0.8433(11) 0.6492(13) 0.4652(4) 0.083(4) Uani 1 1 d . . . . .
H7 H 0.819807 0.627368 0.491688 0.100 Uiso 1 1 calc R U . . .
C15 C 0.8298(12) 0.7803(15) 0.4479(5) 0.100(5) Uani 1 1 d . . . . .
H10 H 0.798018 0.846603 0.462996 0.120 Uiso 1 1 calc R U . . .
C16 C 0.8626(11) 0.8155(15) 0.4084(5) 0.086(4) Uani 1 1 d . . . . .
H9 H 0.850762 0.904005 0.396589 0.103 Uiso 1 1 calc R U . . .
C17 C 0.9121(10) 0.7213(13) 0.3867(4) 0.069(3) Uani 1 1 d . . . . .
H8 H 0.935471 0.746125 0.360487 0.083 Uiso 1 1 calc R U . . .
C18 C 0.6239(7) -0.1688(9) 0.7413(3) 0.040(2) Uani 1 1 d . . . . .
H4 H 0.595904 -0.098854 0.720125 0.060 Uiso 1 1 calc R U . . .
H5 H 0.607730 -0.147567 0.770408 0.060 Uiso 1 1 calc R U . . .
H6 H 0.595111 -0.256922 0.731429 0.060 Uiso 1 1 calc R U . . .
C19 C 0.8595(10) -0.3242(12) 0.7081(4) 0.071(3) Uani 1 1 d . . . . .
H1 H 0.838537 -0.415140 0.715282 0.107 Uiso 1 1 calc R U . . .
H2 H 0.932755 -0.317616 0.715153 0.107 Uiso 1 1 calc R U . . .
H3 H 0.837077 -0.306775 0.676497 0.107 Uiso 1 1 calc R U . . .
C20 C 0.8929(9) -0.0646(12) 0.7966(4) 0.071(3) Uani 1 1 d . . . . .
H17 H 0.912526 -0.122259 0.822647 0.106 Uiso 1 1 calc R U . . .
H18 H 0.858149 0.015856 0.804886 0.106 Uiso 1 1 calc R U . . .
H19 H 0.952824 -0.036875 0.785171 0.106 Uiso 1 1 calc R U . . .
N1 N 0.8862(8) 0.2548(10) 0.5155(3) 0.058(2) Uani 1 1 d D . . . .
N2 N 0.8730(7) 0.3787(9) 0.4985(3) 0.053(2) Uani 1 1 d . . . . .
O1 O 0.8097(7) -0.0305(8) 0.6928(3) 0.077(2) Uani 1 1 d . . . . .
O2 O 0.7149(7) 0.1538(7) 0.6988(2) 0.065(2) Uani 1 1 d . . . . .
O3 O 0.9758(7) 0.1861(9) 0.4504(3) 0.077(2) Uani 1 1 d . . . . .
Sn1 Sn 0.79380(5) -0.17626(7) 0.74618(2) 0.0440(3) Uani 1 1 d . . . . .
H1A H 0.918(14) 0.203(18) 0.500(6) 0.21(10) Uiso 1 1 d 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'
Sn Sn -0.6537 1.4246 '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
O2 C1 O1 123.9(9) . .
O2 C1 C2 121.3(9) . .
O1 C1 C2 114.7(9) . .
C3 C2 C7 118.0(9) . .
C3 C2 C1 120.2(9) . .
C7 C2 C1 121.8(9) . .
C2 C3 C4 121.9(9) . .
C2 C3 H13 119.0 . .
C4 C3 H13 119.0 . .
C3 C4 C5 118.6(9) . .
C3 C4 H14 120.7 . .
C5 C4 H14 120.7 . .
C6 C5 N1 122.7(9) . .
C6 C5 C4 120.8(9) . .
N1 C5 C4 116.4(9) . .
C5 C6 C7 119.7(9) . .
C5 C6 H15 120.1 . .
C7 C6 H15 120.1 . .
C6 C7 C2 121.0(9) . .
C6 C7 H16 119.5 . .
C2 C7 H16 119.5 . .
N2 C8 C13 116.9(9) . .
N2 C8 C9 124.2(10) . .
C13 C8 C9 118.9(9) . .
O3 C9 C10 121.3(10) . .
O3 C9 C8 120.6(10) . .
C10 C9 C8 118.1(11) . .
C11 C10 C9 121.0(11) . .
C11 C10 H12 119.5 . .
C9 C10 H12 119.5 . .
C10 C11 C12 124.2(10) . .
C10 C11 H11 117.9 . .
C12 C11 H11 117.9 . .
C17 C12 C11 122.0(10) . .
C17 C12 C13 119.3(11) . .
C11 C12 C13 118.7(10) . .
C14 C13 C12 118.5(11) . .
C14 C13 C8 122.3(9) . .
C12 C13 C8 119.1(10) . .
C15 C14 C13 120.5(11) . .
C15 C14 H7 119.7 . .
C13 C14 H7 119.7 . .
C14 C15 C16 121.1(13) . .
C14 C15 H10 119.4 . .
C16 C15 H10 119.4 . .
C17 C16 C15 120.2(13) . .
C17 C16 H9 119.9 . .
C15 C16 H9 119.9 . .
C16 C17 C12 120.3(11) . .
C16 C17 H8 119.9 . .
C12 C17 H8 119.9 . .
Sn1 C18 H4 109.5 . .
Sn1 C18 H5 109.5 . .
H4 C18 H5 109.5 . .
Sn1 C18 H6 109.5 . .
H4 C18 H6 109.5 . .
H5 C18 H6 109.5 . .
Sn1 C19 H1 109.5 . .
Sn1 C19 H2 109.5 . .
H1 C19 H2 109.5 . .
Sn1 C19 H3 109.5 . .
H1 C19 H3 109.5 . .
H2 C19 H3 109.5 . .
Sn1 C20 H17 109.5 . .
Sn1 C20 H18 109.5 . .
H17 C20 H18 109.5 . .
Sn1 C20 H19 109.5 . .
H17 C20 H19 109.5 . .
H18 C20 H19 109.5 . .
N2 N1 C5 122.5(9) . .
N2 N1 H1A 112(10) . .
C5 N1 H1A 126(10) . .
N1 N2 C8 119.2(9) . .
C1 O1 Sn1 137.2(7) . .
C1 O2 Sn1 145.2(7) . 4_656
C19 Sn1 C20 118.0(5) . .
C19 Sn1 O1 86.3(4) . .
C20 Sn1 O1 94.0(4) . .
C19 Sn1 C18 119.6(4) . .
C20 Sn1 C18 121.4(4) . .
O1 Sn1 C18 99.2(3) . .
C19 Sn1 O2 89.2(4) . 4_646
C20 Sn1 O2 87.3(4) . 4_646
O1 Sn1 O2 175.4(3) . 4_646
C18 Sn1 O2 83.9(3) . 4_646
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.246(11) .
C1 O1 1.256(12) .
C1 C2 1.484(12) .
C2 C3 1.385(13) .
C2 C7 1.398(13) .
C3 C4 1.385(13) .
C3 H13 0.9300 .
C4 C5 1.392(13) .
C4 H14 0.9300 .
C5 C6 1.377(13) .
C5 N1 1.384(12) .
C6 C7 1.381(13) .
C6 H15 0.9300 .
C7 H16 0.9300 .
C8 N2 1.320(12) .
C8 C13 1.468(15) .
C8 C9 1.470(14) .
C9 O3 1.259(13) .
C9 C10 1.433(15) .
C10 C11 1.337(16) .
C10 H12 0.9300 .
C11 C12 1.418(16) .
C11 H11 0.9300 .
C12 C17 1.407(16) .
C12 C13 1.422(13) .
C13 C14 1.383(15) .
C14 C15 1.372(17) .
C14 H7 0.9300 .
C15 C16 1.381(17) .
C15 H10 0.9300 .
C16 C17 1.357(17) .
C16 H9 0.9300 .
C17 H8 0.9300 .
C18 Sn1 2.236(9) .
C18 H4 0.9600 .
C18 H5 0.9600 .
C18 H6 0.9600 .
C19 Sn1 2.117(11) .
C19 H1 0.9600 .
C19 H2 0.9600 .
C19 H3 0.9600 .
C20 Sn1 2.122(11) .
C20 H17 0.9600 .
C20 H18 0.9600 .
C20 H19 0.9600 .
N1 N2 1.304(12) .
N1 H1A 0.85(2) .
O1 Sn1 2.177(7) .
O2 Sn1 2.352(7) 4_656
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 H1A O3 0.85(2) 1.80(12) 2.555(12) 147(20) . yes
C4 H14 O3 0.93 2.54 3.384(13) 151.7 5_756 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
O2 C1 C2 C3 -168.3(10) . . . .
O1 C1 C2 C3 9.2(15) . . . .
O2 C1 C2 C7 11.0(15) . . . .
O1 C1 C2 C7 -171.4(10) . . . .
C7 C2 C3 C4 1.6(16) . . . .
C1 C2 C3 C4 -179.0(10) . . . .
C2 C3 C4 C5 -1.7(17) . . . .
C3 C4 C5 C6 2.4(16) . . . .
C3 C4 C5 N1 177.9(10) . . . .
N1 C5 C6 C7 -178.2(10) . . . .
C4 C5 C6 C7 -2.9(17) . . . .
C5 C6 C7 C2 2.8(17) . . . .
C3 C2 C7 C6 -2.1(16) . . . .
C1 C2 C7 C6 178.5(10) . . . .
N2 C8 C9 O3 1.4(18) . . . .
C13 C8 C9 O3 -178.2(11) . . . .
N2 C8 C9 C10 -177.8(11) . . . .
C13 C8 C9 C10 2.6(16) . . . .
O3 C9 C10 C11 178.1(12) . . . .
C8 C9 C10 C11 -2.7(18) . . . .
C9 C10 C11 C12 1(2) . . . .
C10 C11 C12 C17 -180.0(12) . . . .
C10 C11 C12 C13 1.8(19) . . . .
C17 C12 C13 C14 -1.7(17) . . . .
C11 C12 C13 C14 176.6(12) . . . .
C17 C12 C13 C8 179.9(10) . . . .
C11 C12 C13 C8 -1.8(16) . . . .
N2 C8 C13 C14 1.7(17) . . . .
C9 C8 C13 C14 -178.7(12) . . . .
N2 C8 C13 C12 180.0(10) . . . .
C9 C8 C13 C12 -0.4(15) . . . .
C12 C13 C14 C15 1(2) . . . .
C8 C13 C14 C15 179.4(13) . . . .
C13 C14 C15 C16 1(3) . . . .
C14 C15 C16 C17 -2(3) . . . .
C15 C16 C17 C12 1(2) . . . .
C11 C12 C17 C16 -177.8(12) . . . .
C13 C12 C17 C16 0.4(18) . . . .
C6 C5 N1 N2 -0.9(17) . . . .
C4 C5 N1 N2 -176.4(10) . . . .
C5 N1 N2 C8 178.4(10) . . . .
C13 C8 N2 N1 -180.0(10) . . . .
C9 C8 N2 N1 0.4(17) . . . .
O2 C1 O1 Sn1 5.6(18) . . . .
C2 C1 O1 Sn1 -171.9(8) . . . .
O1 C1 O2 Sn1 89.6(14) . . . 4_656
C2 C1 O2 Sn1 -93.1(13) . . . 4_656
