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#$Date: 2023-07-05 13:52:48 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284964 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159284.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_7159284
loop_
_publ_author_name
'Santos, Camila O.'
'Passos, Saulo T. A.'
'Sorto, Jenny E. P.'
'Machado, Daniel F. S.'
'Correa, Jose R.'
'da Silva Júnior, Eufrânio N'
'Rodrigues, Marcelo O.'
'Neto, Brenno A. D.'
_publ_section_title
;
 Sensitive hydrazine detection and quantification with a fluorescent
 benzothiadiazole sensor: selective lipid droplets and in vivo
 imaging.
;
_journal_issue                   22
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4606
_journal_page_last               4619
_journal_paper_doi               10.1039/d3ob00007a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C20 H14 N2 O2 S'
_chemical_formula_weight         348.41
_chemical_name_systematic
'Sensitive Hydrazine Detection and Quantification with a Fluorescent Benzothiadiazole Probe: Selective Cellular and Multicellular Imaging.'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-02-22 deposited with the CCDC.	2023-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.913(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0010(17)
_cell_length_b                   17.669(3)
_cell_length_c                   9.0754(16)
_cell_measurement_reflns_used    1096
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.14
_cell_measurement_theta_min      3.01
_cell_volume                     1584.3(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Ortep3 (Farrugia,1997)'
_computing_publication_material  'WinGX-Routine (Farrugia,1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_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  0.0538
_diffrn_reflns_av_unetI/netI     0.1416
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8824
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.503
_diffrn_reflns_theta_min         2.547
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(Clark, R. C. & Reid, J. S. (1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.913
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         5830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.2507
_refine_ls_R_factor_gt           0.1071
_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)+(0.1453P)²+3.0240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3109
_refine_ls_wR_factor_ref         0.3918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2119
_reflns_number_total             5830
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00007a2.cif
_cod_data_source_block           C34-48
_cod_depositor_comments          'Adding full bibliography for 7159284.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159284
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_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_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
S1 S 0.75151(17) 0.45866(9) 0.45328(17) 0.0541(5) Uani 1 1 d . . . . .
O1 O 0.2210(4) 0.6403(3) -0.1913(4) 0.0519(11) Uani 1 1 d . . . . .
N1 N 0.7728(5) 0.5066(3) 0.6066(5) 0.0472(11) Uani 1 1 d . . . . .
N2 N 0.6393(5) 0.5089(3) 0.3516(5) 0.0483(12) Uani 1 1 d . . . . .
C14 C 0.4387(5) 0.6307(3) 0.2367(6) 0.0406(12) Uani 1 1 d . . . . .
C7 C 0.7415(5) 0.6185(3) 0.8475(6) 0.0387(12) Uani 1 1 d . . . . .
C17 C 0.2864(5) 0.6397(3) -0.0477(6) 0.0406(12) Uani 1 1 d . . . . .
C2 C 0.6871(5) 0.5654(3) 0.5842(6) 0.0399(12) Uani 1 1 d . . . . .
C15 C 0.4892(5) 0.6047(3) 0.1133(6) 0.0414(12) Uani 1 1 d . . . . .
H15 H 0.5758 0.5842 0.1251 0.050 Uiso 1 1 calc R U . . .
C3 C 0.6118(5) 0.5681(3) 0.4354(6) 0.0392(11) Uani 1 1 d . . . . .
C4 C 0.5184(5) 0.6271(3) 0.3908(6) 0.0400(12) Uani 1 1 d . . . . .
C1 C 0.6693(5) 0.6217(3) 0.6932(6) 0.0395(12) Uani 1 1 d . . . . .
O2 O 0.9734(7) 0.6608(4) 1.3797(6) 0.0915(19) Uani 1 1 d . . . . .
C8 C 0.7790(6) 0.5495(3) 0.9189(6) 0.0454(13) Uani 1 1 d . . . . .
H8 H 0.7589 0.5041 0.8681 0.055 Uiso 1 1 calc R U . . .
C12 C 0.7721(5) 0.6851(3) 0.9292(6) 0.0437(13) Uani 1 1 d . . . . .
H12 H 0.7482 0.7316 0.8850 0.052 Uiso 1 1 calc R U . . .
C10 C 0.8748(5) 0.6142(3) 1.1426(6) 0.0422(12) Uani 1 1 d . . . . .
C16 C 0.4140(5) 0.6085(3) -0.0273(6) 0.0446(13) Uani 1 1 d . . . . .
H16 H 0.4497 0.5898 -0.1088 0.054 Uiso 1 1 calc R U . . .
C19 C 0.3101(6) 0.6630(4) 0.2135(7) 0.0481(14) Uani 1 1 d . . . . .
H19 H 0.2746 0.6822 0.2948 0.058 Uiso 1 1 calc R U . . .
C6 C 0.5786(6) 0.6770(3) 0.6432(7) 0.0473(13) Uani 1 1 d . . . . .
H6 H 0.5627 0.7148 0.7097 0.057 Uiso 1 1 calc R U . . .
C11 C 0.8376(6) 0.6825(3) 1.0750(7) 0.0472(13) Uani 1 1 d . . . . .
H11 H 0.8567 0.7273 1.1279 0.057 Uiso 1 1 calc R U . . .
C18 C 0.2341(5) 0.6672(3) 0.0741(7) 0.0471(14) Uani 1 1 d . . . . .
H18 H 0.1481 0.6885 0.0617 0.057 Uiso 1 1 calc R U . . .
C13 C 0.9439(7) 0.6090(4) 1.2970(8) 0.0566(16) Uani 1 1 d . . . . .
H13 H 0.9669 0.5609 1.3337 0.068 Uiso 1 1 calc R U . . .
C9 C 0.8446(6) 0.5486(3) 1.0622(6) 0.0470(13) Uani 1 1 d . . . . .
H9 H 0.8697 0.5024 1.1071 0.056 Uiso 1 1 calc R U . . .
C5 C 0.5073(6) 0.6802(4) 0.4967(7) 0.0489(14) Uani 1 1 d . . . . .
H5 H 0.4495 0.7210 0.4709 0.059 Uiso 1 1 calc R U . . .
C20 C 0.0855(6) 0.6650(4) -0.2186(8) 0.0648(19) Uani 1 1 d . . . . .
H20A H 0.0499 0.6581 -0.3222 0.097 Uiso 1 1 calc R U . . .
H20B H 0.0815 0.7177 -0.1935 0.097 Uiso 1 1 calc R U . . .
H20C H 0.0328 0.6362 -0.1588 0.097 Uiso 1 1 calc R U . . .
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
_geom_angle_publ_flag
N2 S1 N1 101.1(3) . . ?
C17 O1 C20 118.4(5) . . ?
C2 N1 S1 106.2(4) . . ?
C3 N2 S1 106.9(4) . . ?
C15 C14 C19 117.4(5) . . ?
C15 C14 C4 122.3(5) . . ?
C19 C14 C4 120.3(5) . . ?
C12 C7 C8 117.7(5) . . ?
C12 C7 C1 120.3(5) . . ?
C8 C7 C1 121.9(5) . . ?
O1 C17 C18 125.2(5) . . ?
O1 C17 C16 115.4(5) . . ?
C18 C17 C16 119.4(5) . . ?
N1 C2 C1 125.3(5) . . ?
N1 C2 C3 113.4(5) . . ?
C1 C2 C3 121.4(5) . . ?
C14 C15 C16 121.4(5) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
N2 C3 C4 126.4(5) . . ?
N2 C3 C2 112.3(5) . . ?
C4 C3 C2 121.2(5) . . ?
C5 C4 C3 115.4(5) . . ?
C5 C4 C14 122.6(5) . . ?
C3 C4 C14 122.0(5) . . ?
C6 C1 C2 114.6(5) . . ?
C6 C1 C7 123.2(5) . . ?
C2 C1 C7 122.2(5) . . ?
C9 C8 C7 120.3(5) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C11 C12 C7 120.8(5) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C11 C10 C9 118.6(5) . . ?
C11 C10 C13 122.3(6) . . ?
C9 C10 C13 119.1(5) . . ?
C15 C16 C17 120.4(5) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C19 C14 121.8(5) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 119.1 . . ?
C1 C6 C5 123.8(5) . . ?
C1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
C10 C11 C12 120.6(6) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C19 C18 C17 119.6(5) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
O2 C13 C10 126.1(7) . . ?
O2 C13 H13 117.0 . . ?
C10 C13 H13 117.0 . . ?
C8 C9 C10 122.0(6) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C4 C5 C6 123.6(6) . . ?
C4 C5 H5 118.2 . . ?
C6 C5 H5 118.2 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 N2 1.606(5) . ?
S1 N1 1.615(5) . ?
O1 C17 1.365(6) . ?
O1 C20 1.409(7) . ?
N1 C2 1.342(7) . ?
N2 C3 1.347(7) . ?
C14 C15 1.377(8) . ?
C14 C19 1.392(7) . ?
C14 C4 1.500(7) . ?
C7 C12 1.400(8) . ?
C7 C8 1.404(8) . ?
C7 C1 1.474(7) . ?
C17 C18 1.382(8) . ?
C17 C16 1.376(7) . ?
C2 C1 1.434(8) . ?
C2 C3 1.442(7) . ?
C15 C16 1.379(7) . ?
C15 H15 0.9300 . ?
C3 C4 1.416(7) . ?
C4 C5 1.361(8) . ?
C1 C6 1.362(8) . ?
O2 C13 1.191(8) . ?
C8 C9 1.363(8) . ?
C8 H8 0.9300 . ?
C12 C11 1.383(8) . ?
C12 H12 0.9300 . ?
C10 C11 1.379(8) . ?
C10 C9 1.379(8) . ?
C10 C13 1.466(8) . ?
C16 H16 0.9300 . ?
C19 C18 1.374(8) . ?
C19 H19 0.9300 . ?
C6 C5 1.409(8) . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C18 H18 0.9300 . ?
C13 H13 0.9300 . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
