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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/63/7106319.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_7106319
loop_
_publ_author_name
'Koji Tsukamoto'
'Yuka Shinohara'
'Shogo Iwasaki'
'Hatsuo Maeda'
_publ_section_title
;
 A coumarin-based fluorescent probe for Hg2+ and Ag+ with an
 N'-acetylthioureido group as a fluorescence switch
;
_journal_name_full               Chem.Commun.
_journal_page_first              5073
_journal_paper_doi               10.1039/c1cc10933b
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C12 H12 N2 O3 S'
_chemical_formula_sum            'C12 H12 N2 O3 S'
_chemical_formula_weight         264.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.804(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9012(1)
_cell_length_b                   16.4201(3)
_cell_length_c                   9.3473(2)
_cell_measurement_reflns_used    12381
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      136.47
_cell_measurement_theta_min      9.47
_cell_volume                     1211.25(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 2003)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEPIII (Johnson et al., 1996)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13375
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         5.39
_exptl_absorpt_coefficient_mu    2.416
_exptl_absorpt_correction_T_max  0.718
_exptl_absorpt_correction_T_min  0.353
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(NUMABS; Higashi, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0266(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0546P)²+0.2697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                2030
_reflns_number_total             2217
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10933b.txt
_cod_data_source_block           et5
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7106319
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.61358(5) 0.23506(2) 0.40177(5) 0.0433(2) Uani 1 1 d . . .
O1 O 0.86994(16) -0.04404(9) 0.59176(16) 0.0604(4) Uani 1 1 d . . .
O2 O 0.65404(13) -0.05561(7) 0.72827(12) 0.0406(3) Uani 1 1 d . . .
O3 O 0.19722(16) -0.09216(8) 1.03300(15) 0.0524(4) Uani 1 1 d . . .
H3O H 0.248(3) -0.1363(17) 1.052(3) 0.079 Uiso 1 1 d . . .
N1 N 0.78481(18) 0.09937(8) 0.48504(16) 0.0411(4) Uani 1 1 d . . .
H1N H 0.867(2) 0.0701(13) 0.476(2) 0.049 Uiso 1 1 d . . .
N2 N 0.91388(18) 0.18004(8) 0.33069(16) 0.0406(4) Uani 1 1 d . . .
H2N H 0.995(2) 0.1445(13) 0.343(2) 0.049 Uiso 1 1 d . . .
C1 C 0.7404(2) -0.01334(10) 0.63259(18) 0.0400(4) Uani 1 1 d . . .
C2 C 0.6761(2) 0.06526(9) 0.58240(18) 0.0363(4) Uani 1 1 d . . .
C3 C 0.5305(2) 0.09441(10) 0.63279(19) 0.0415(4) Uani 1 1 d . . .
H3 H 0.4889 0.1447 0.6018 0.050 Uiso 1 1 calc R . .
C4 C 0.4406(2) 0.04792(9) 0.73376(18) 0.0385(4) Uani 1 1 d . . .
C5 C 0.2884(2) 0.07231(11) 0.7916(2) 0.0513(5) Uani 1 1 d . . .
H5 H 0.2404 0.1219 0.7635 0.062 Uiso 1 1 calc R . .
C6 C 0.2085(2) 0.02497(11) 0.8885(2) 0.0513(5) Uani 1 1 d . . .
H6 H 0.1071 0.0424 0.9248 0.062 Uiso 1 1 calc R . .
C7 C 0.2792(2) -0.04928(10) 0.93272(19) 0.0403(4) Uani 1 1 d . . .
C8 C 0.4283(2) -0.07606(9) 0.87724(18) 0.0373(4) Uani 1 1 d . . .
H8 H 0.4757 -0.1258 0.9049 0.045 Uiso 1 1 calc R . .
C9 C 0.50467(18) -0.02700(9) 0.77994(17) 0.0341(4) Uani 1 1 d . . .
C10 C 0.7768(2) 0.16913(9) 0.40614(17) 0.0345(4) Uani 1 1 d . . .
C11 C 0.9423(2) 0.24750(11) 0.2342(2) 0.0454(4) Uani 1 1 d . . .
H11A H 0.9600 0.2973 0.2887 0.054 Uiso 1 1 calc R . .
H11B H 0.8437 0.2549 0.1695 0.054 Uiso 1 1 calc R . .
C12 C 1.0955(3) 0.22995(12) 0.1496(2) 0.0542(5) Uani 1 1 d . . .
H12A H 1.1927 0.2227 0.2141 0.081 Uiso 1 1 calc R . .
H12B H 1.1151 0.2747 0.0865 0.081 Uiso 1 1 calc R . .
H12C H 1.0765 0.1812 0.0943 0.081 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C1 O2 C9 121.87(13) . . ?
C7 O3 H3O 110.4(17) . . ?
C10 N1 C2 132.49(14) . . ?
C10 N1 H1N 116.9(14) . . ?
C2 N1 H1N 110.6(14) . . ?
C10 N2 C11 125.82(15) . . ?
C10 N2 H2N 116.9(13) . . ?
C11 N2 H2N 117.2(13) . . ?
O1 C1 O2 117.13(15) . . ?
O1 C1 C2 123.42(15) . . ?
O2 C1 C2 119.44(13) . . ?
C3 C2 N1 130.17(15) . . ?
C3 C2 C1 119.40(14) . . ?
N1 C2 C1 110.42(13) . . ?
C2 C3 C4 119.98(15) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C9 C4 C5 116.05(15) . . ?
C9 C4 C3 119.49(14) . . ?
C5 C4 C3 124.46(15) . . ?
C6 C5 C4 121.67(16) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 119.99(16) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
O3 C7 C8 122.47(15) . . ?
O3 C7 C6 117.28(15) . . ?
C8 C7 C6 120.24(15) . . ?
C9 C8 C7 118.10(15) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C8 C9 O2 116.26(14) . . ?
C8 C9 C4 123.94(14) . . ?
O2 C9 C4 119.80(14) . . ?
N2 C10 N1 112.47(14) . . ?
N2 C10 S1 122.84(12) . . ?
N1 C10 S1 124.70(12) . . ?
N2 C11 C12 109.43(15) . . ?
N2 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
N2 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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
S1 C10 1.6829(16) . ?
O1 C1 1.2189(19) . ?
O2 C1 1.3443(19) . ?
O2 C9 1.3793(17) . ?
O3 C7 1.362(2) . ?
O3 H3O 0.84(3) . ?
N1 C10 1.362(2) . ?
N1 C2 1.399(2) . ?
N1 H1N 0.81(2) . ?
N2 C10 1.333(2) . ?
N2 C11 1.453(2) . ?
N2 H2N 0.87(2) . ?
C1 C2 1.456(2) . ?
C2 C3 1.352(2) . ?
C3 C4 1.429(2) . ?
C3 H3 0.9300 . ?
C4 C9 1.391(2) . ?
C4 C5 1.401(2) . ?
C5 C6 1.371(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(2) . ?
C8 C9 1.376(2) . ?
C8 H8 0.9300 . ?
C11 C12 1.506(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653279
2 PubChem 101796688
