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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/1/56/59/1565921.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.
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data_1565921
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         'C17 H12 N2 O3'
_chemical_formula_sum            'C17 H12 N2 O3'
_chemical_formula_weight         292.29
_chemical_name_systematic        '4-(2-hydroxynaphthylazo) benzoic acid'
_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                 90.235(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.168(3)
_cell_length_b                   5.0685(10)
_cell_length_c                   35.807(7)
_cell_measurement_reflns_used    1063
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.55
_cell_measurement_theta_min      2.27
_cell_volume                     2752.8(9)
_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-2018/3 (Sheldrick, 2018)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.994
_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  0.1040
_diffrn_reflns_av_unetI/netI     0.1061
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            11859
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.304
_diffrn_reflns_theta_min         2.275
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (bruker, 2004)'
_exptl_crystal_colour            RED
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.924
_refine_ls_R_factor_all          0.1854
_refine_ls_R_factor_gt           0.0493
_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)+(0.0514P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                909
_reflns_number_total             2490
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2019-498-119172.cif
_cod_data_source_block           KSS15
_cod_original_cell_volume        2752.8(10)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1565921
_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   0.981
_shelx_estimated_absorpt_t_max   0.990
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 0.4369(2) -0.2176(7) 0.52430(10) 0.0539(10) Uani 1 1 d . . . . .
C2 C 0.3903(2) -0.0080(6) 0.54476(9) 0.0464(9) Uani 1 1 d . . . . .
C3 C 0.3018(2) 0.0396(7) 0.53841(9) 0.0555(10) Uani 1 1 d . . . . .
H3 H 0.271459 -0.060297 0.520759 0.067 Uiso 1 1 calc R U . . .
C4 C 0.2579(2) 0.2336(7) 0.55794(9) 0.0547(9) Uani 1 1 d . . . . .
H4 H 0.198208 0.263129 0.553680 0.066 Uiso 1 1 calc R U . . .
C5 C 0.3035(2) 0.3845(7) 0.58401(9) 0.0475(9) Uani 1 1 d . . . . .
C6 C 0.3921(2) 0.3401(7) 0.59041(9) 0.0556(10) Uani 1 1 d . . . . .
H6 H 0.422796 0.441436 0.607757 0.067 Uiso 1 1 calc R U . . .
C7 C 0.4343(2) 0.1444(7) 0.57087(9) 0.0558(9) Uani 1 1 d . . . . .
H7 H 0.493852 0.113831 0.575297 0.067 Uiso 1 1 calc R U . . .
C8 C 0.2480(2) 0.9104(7) 0.64562(9) 0.0521(9) Uani 1 1 d . . . . .
C9 C 0.1549(3) 0.9535(8) 0.63904(11) 0.0680(11) Uani 1 1 d . . . . .
C10 C 0.1126(3) 1.1578(9) 0.66059(13) 0.0886(14) Uani 1 1 d . . . . .
H10 H 0.052511 1.187853 0.657404 0.106 Uiso 1 1 calc R U . . .
C11 C 0.1579(3) 1.3050(8) 0.68506(12) 0.0836(13) Uani 1 1 d . . . . .
H11 H 0.128221 1.435992 0.698151 0.100 Uiso 1 1 calc R U . . .
C12 C 0.2494(3) 1.2694(7) 0.69184(10) 0.0577(10) Uani 1 1 d . . . . .
C13 C 0.2949(3) 1.4290(8) 0.71747(10) 0.0736(12) Uani 1 1 d . . . . .
H13 H 0.264444 1.559197 0.730375 0.088 Uiso 1 1 calc R U . . .
C14 C 0.3823(3) 1.3974(8) 0.72382(11) 0.0844(13) Uani 1 1 d . . . . .
H14 H 0.411395 1.504273 0.741020 0.101 Uiso 1 1 calc R U . . .
C15 C 0.4282(3) 1.2045(8) 0.70451(12) 0.0892(14) Uani 1 1 d . . . . .
H15 H 0.488371 1.182966 0.708640 0.107 Uiso 1 1 calc R U . . .
C16 C 0.3849(3) 1.0440(8) 0.67913(11) 0.0731(12) Uani 1 1 d . . . . .
H16 H 0.416325 0.914522 0.666469 0.088 Uiso 1 1 calc R U . . .
C17 C 0.2951(2) 1.0736(7) 0.67228(9) 0.0525(9) Uani 1 1 d . . . . .
N1 N 0.29524(17) 0.7282(6) 0.62785(8) 0.0531(8) Uani 1 1 d . . . . .
N2 N 0.2553(2) 0.5785(6) 0.60307(8) 0.0559(8) Uani 1 1 d . . . . .
O1 O 0.51790(15) -0.2549(4) 0.53191(6) 0.0668(7) Uani 1 1 d . . . . .
H1A H 0.536577 -0.378765 0.519522 0.100 Uiso 1 1 calc R U . . .
O2 O 0.39548(14) -0.3517(4) 0.49951(6) 0.0656(7) Uani 1 1 d . . . . .
O3 O 0.11089(16) 0.8175(5) 0.61603(8) 0.0881(9) Uani 1 1 d . . . . .
H2A H 0.190(3) 0.618(8) 0.5991(11) 0.134(17) Uiso 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'
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
O1 C1 O2 122.7(3) . .
O1 C1 C2 117.8(3) . .
O2 C1 C2 119.5(3) . .
C3 C2 C7 118.7(3) . .
C3 C2 C1 120.8(3) . .
C7 C2 C1 120.5(3) . .
C4 C3 C2 120.8(3) . .
C4 C3 H3 119.6 . .
C2 C3 H3 119.6 . .
C3 C4 C5 119.6(3) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
C6 C5 C4 120.2(3) . .
C6 C5 N2 122.9(3) . .
C4 C5 N2 116.9(3) . .
C7 C6 C5 119.3(3) . .
C7 C6 H6 120.4 . .
C5 C6 H6 120.4 . .
C6 C7 C2 121.5(3) . .
C6 C7 H7 119.2 . .
C2 C7 H7 119.2 . .
N1 C8 C9 123.6(3) . .
N1 C8 C17 116.4(3) . .
C9 C8 C17 120.0(4) . .
O3 C9 C10 120.3(4) . .
O3 C9 C8 122.4(4) . .
C10 C9 C8 117.2(4) . .
C11 C10 C9 121.4(4) . .
C11 C10 H10 119.3 . .
C9 C10 H10 119.3 . .
C10 C11 C12 122.7(4) . .
C10 C11 H11 118.6 . .
C12 C11 H11 118.6 . .
C17 C12 C13 119.5(4) . .
C17 C12 C11 119.4(4) . .
C13 C12 C11 121.1(4) . .
C14 C13 C12 121.4(4) . .
C14 C13 H13 119.3 . .
C12 C13 H13 119.3 . .
C13 C14 C15 119.5(4) . .
C13 C14 H14 120.2 . .
C15 C14 H14 120.2 . .
C16 C15 C14 120.3(4) . .
C16 C15 H15 119.9 . .
C14 C15 H15 119.9 . .
C15 C16 C17 121.0(4) . .
C15 C16 H16 119.5 . .
C17 C16 H16 119.5 . .
C16 C17 C12 118.4(4) . .
C16 C17 C8 122.3(4) . .
C12 C17 C8 119.3(3) . .
N2 N1 C8 118.4(3) . .
N1 N2 C5 119.5(3) . .
N1 N2 H2A 115(2) . .
C5 N2 H2A 125(2) . .
C1 O1 H1A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.271(3) .
C1 O2 1.281(3) .
C1 C2 1.473(4) .
C2 C3 1.381(4) .
C2 C7 1.383(4) .
C3 C4 1.379(4) .
C3 H3 0.9300 .
C4 C5 1.390(4) .
C4 H4 0.9300 .
C5 C6 1.380(4) .
C5 N2 1.404(4) .
C6 C7 1.373(4) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 N1 1.332(4) .
C8 C9 1.447(4) .
C8 C17 1.450(4) .
C9 O3 1.263(4) .
C9 C10 1.444(5) .
C10 C11 1.339(5) .
C10 H10 0.9300 .
C11 C12 1.419(5) .
C11 H11 0.9300 .
C12 C17 1.401(4) .
C12 C13 1.403(5) .
C13 C14 1.354(5) .
C13 H13 0.9300 .
C14 C15 1.386(5) .
C14 H14 0.9300 .
C15 C16 1.383(5) .
C15 H15 0.9300 .
C16 C17 1.391(4) .
C16 H16 0.9300 .
N1 N2 1.314(3) .
N2 H2A 1.02(4) .
O1 H1A 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
_geom_hbond_publ_flag
O1 H1A O2 0.82 1.84 2.642(3) 164.2 5_646 yes
N2 H2A O3 1.02(4) 1.68(4) 2.547(4) 139(3) . 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
O1 C1 C2 C3 -178.7(3) . . . .
O2 C1 C2 C3 2.1(5) . . . .
O1 C1 C2 C7 1.1(5) . . . .
O2 C1 C2 C7 -178.1(3) . . . .
C7 C2 C3 C4 -0.6(5) . . . .
C1 C2 C3 C4 179.2(3) . . . .
C2 C3 C4 C5 0.7(5) . . . .
C3 C4 C5 C6 -0.2(5) . . . .
C3 C4 C5 N2 -179.8(3) . . . .
C4 C5 C6 C7 -0.3(5) . . . .
N2 C5 C6 C7 179.3(3) . . . .
C5 C6 C7 C2 0.4(5) . . . .
C3 C2 C7 C6 0.1(5) . . . .
C1 C2 C7 C6 -179.7(3) . . . .
N1 C8 C9 O3 0.9(6) . . . .
C17 C8 C9 O3 179.7(3) . . . .
N1 C8 C9 C10 179.8(3) . . . .
C17 C8 C9 C10 -1.5(5) . . . .
O3 C9 C10 C11 -179.8(4) . . . .
C8 C9 C10 C11 1.4(6) . . . .
C9 C10 C11 C12 -0.8(7) . . . .
C10 C11 C12 C17 0.2(6) . . . .
C10 C11 C12 C13 179.4(4) . . . .
C17 C12 C13 C14 -0.2(6) . . . .
C11 C12 C13 C14 -179.4(4) . . . .
C12 C13 C14 C15 0.4(6) . . . .
C13 C14 C15 C16 -0.5(6) . . . .
C14 C15 C16 C17 0.5(6) . . . .
C15 C16 C17 C12 -0.3(5) . . . .
C15 C16 C17 C8 179.4(4) . . . .
C13 C12 C17 C16 0.2(5) . . . .
C11 C12 C17 C16 179.4(3) . . . .
C13 C12 C17 C8 -179.6(3) . . . .
C11 C12 C17 C8 -0.3(5) . . . .
N1 C8 C17 C16 0.1(5) . . . .
C9 C8 C17 C16 -178.7(3) . . . .
N1 C8 C17 C12 179.8(3) . . . .
C9 C8 C17 C12 1.0(5) . . . .
C9 C8 N1 N2 -0.3(5) . . . .
C17 C8 N1 N2 -179.1(3) . . . .
C8 N1 N2 C5 -179.9(3) . . . .
C6 C5 N2 N1 0.9(5) . . . .
C4 C5 N2 N1 -179.5(3) . . . .
