#------------------------------------------------------------------------------
#$Date: 2023-11-10 21:21:08 +0200 (Fri, 10 Nov 2023) $
#$Revision: 287519 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557712.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_1557712
loop_
_publ_author_name
'Ila, ?'
'Dani, Reshmi'
'Verma, Surya Pratap'
'Krishnamoorthy, G.'
_publ_section_title
;
 The origin of the longer wavelength emission in
 2-(4-fluorophenylamino)-5-(2,4-dihydroxybenzeno)-1,3,4-thiadiazole and
 its analogue 2-phenylamino-5-(2-hydroxybenzono)-1,3,4-thiadiazole.
;
_journal_issue                   6
_journal_name_full
'Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              844
_journal_page_last               853
_journal_paper_doi               10.1039/c9pp00490d
_journal_volume                  19
_journal_year                    2020
_chemical_formula_sum            'C15 H13 N3 O S'
_chemical_formula_weight         283.34
_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   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-06-08 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.594(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.0137(9)
_cell_length_b                   7.3113(4)
_cell_length_c                   20.1679(9)
_cell_measurement_temperature    293(2)
_cell_volume                     2790.3(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.881
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5965
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.809
_diffrn_reflns_theta_min         2.811
_exptl_absorpt_coefficient_mu    0.230
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             1184
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0418P)²+0.5858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2238
_reflns_number_total             3206
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9pp00490d2.cif
_cod_data_source_block           exp_6280_CCDC1
_cod_depositor_comments
;Adding full bibliography for 1557711--1557712.cif.

 Adding full bibliography for 1557711--1557712.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1557712
_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.
;
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
S8 S 0.55153(3) 0.70797(7) 0.45029(2) 0.04401(17) Uani 1 1 d . . . . .
O19 O 0.41496(8) 0.7282(2) 0.47104(8) 0.0605(4) Uani 1 1 d . . . . .
N11 N 0.61359(9) 0.8038(2) 0.56284(8) 0.0497(5) Uani 1 1 d . . . . .
N12 N 0.68877(9) 0.6892(3) 0.41664(8) 0.0526(5) Uani 1 1 d . . . . .
H12 H 0.731979 0.715530 0.429738 0.063 Uiso 1 1 calc R U . . .
N10 N 0.66678(9) 0.7752(3) 0.52241(8) 0.0517(5) Uani 1 1 d . . . . .
C7 C 0.55058(10) 0.7749(3) 0.53308(9) 0.0391(4) Uani 1 1 d . . . . .
C1 C 0.48712(10) 0.8011(3) 0.56772(10) 0.0417(5) Uani 1 1 d . . . . .
C9 C 0.64216(10) 0.7241(3) 0.46187(10) 0.0438(5) Uani 1 1 d . . . . .
C14 C 0.73660(11) 0.5436(3) 0.32567(10) 0.0481(5) Uani 1 1 d . . . . .
H14 H 0.780544 0.549504 0.350252 0.058 Uiso 1 1 calc R U . . .
C13 C 0.67795(11) 0.6168(3) 0.35184(9) 0.0454(5) Uani 1 1 d . . . . .
C6 C 0.41894(11) 0.7796(3) 0.53603(11) 0.0466(5) Uani 1 1 d . . . . .
C2 C 0.49407(12) 0.8532(3) 0.63433(10) 0.0559(6) Uani 1 1 d . . . . .
H2 H 0.538966 0.867984 0.656437 0.067 Uiso 1 1 calc R U . . .
C5 C 0.36036(12) 0.8096(3) 0.57062(13) 0.0602(6) Uani 1 1 d . . . . .
H5 H 0.315138 0.794601 0.549245 0.072 Uiso 1 1 calc R U . . .
C15 C 0.73063(13) 0.4624(3) 0.26382(11) 0.0565(6) Uani 1 1 d . . . . .
H15 H 0.770312 0.411726 0.247412 0.068 Uiso 1 1 calc R U . . .
C18 C 0.61406(12) 0.6157(4) 0.31291(10) 0.0619(7) Uani 1 1 d . . . . .
H18 H 0.574447 0.668866 0.328595 0.074 Uiso 1 1 calc R U . . .
C16 C 0.66642(14) 0.4558(3) 0.22611(11) 0.0643(7) Uani 1 1 d . . . . .
H16 H 0.662030 0.398311 0.184782 0.077 Uiso 1 1 calc R U . . .
C17 C 0.60905(13) 0.5353(4) 0.25052(11) 0.0699(7) Uani 1 1 d . . . . .
H17 H 0.565818 0.535299 0.224613 0.084 Uiso 1 1 calc R U . . .
C3 C 0.43571(14) 0.8832(4) 0.66809(12) 0.0687(7) Uani 1 1 d . . . . .
H3 H 0.441323 0.918531 0.712598 0.082 Uiso 1 1 calc R U . . .
C4 C 0.36905(14) 0.8611(4) 0.63606(13) 0.0696(7) Uani 1 1 d . . . . .
H4 H 0.329660 0.881282 0.659030 0.083 Uiso 1 1 calc R U . . .
C20 C 0.34782(12) 0.7148(4) 0.43385(13) 0.0739(8) Uani 1 1 d . . . . .
H20A H 0.354022 0.696347 0.387657 0.111 Uiso 1 1 calc R U . . .
H20B H 0.321757 0.825618 0.438817 0.111 Uiso 1 1 calc R U . . .
H20C H 0.322283 0.613392 0.449939 0.111 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
C9 S8 C7 87.39(9) . . ?
C6 O19 C20 119.44(18) . . ?
C7 N11 N10 113.46(16) . . ?
C9 N12 C13 130.53(17) . . ?
C9 N10 N11 112.14(16) . . ?
N11 C7 C1 121.46(18) . . ?
N11 C7 S8 113.08(15) . . ?
C1 C7 S8 125.46(15) . . ?
C2 C1 C6 118.0(2) . . ?
C2 C1 C7 119.45(19) . . ?
C6 C1 C7 122.54(19) . . ?
N10 C9 N12 118.68(18) . . ?
N10 C9 S8 113.94(15) . . ?
N12 C9 S8 127.38(15) . . ?
C15 C14 C13 120.9(2) . . ?
C18 C13 C14 118.49(19) . . ?
C18 C13 N12 124.86(19) . . ?
C14 C13 N12 116.65(18) . . ?
O19 C6 C5 123.8(2) . . ?
O19 C6 C1 115.74(19) . . ?
C5 C6 C1 120.4(2) . . ?
C3 C2 C1 121.1(2) . . ?
C4 C5 C6 120.1(2) . . ?
C16 C15 C14 120.5(2) . . ?
C13 C18 C17 119.9(2) . . ?
C17 C16 C15 118.8(2) . . ?
C16 C17 C18 121.4(2) . . ?
C4 C3 C2 120.0(2) . . ?
C5 C4 C3 120.3(2) . . ?
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
S8 C9 1.720(2) . ?
S8 C7 1.7416(19) . ?
O19 C6 1.358(2) . ?
O19 C20 1.420(2) . ?
N11 C7 1.304(2) . ?
N11 N10 1.376(2) . ?
N12 C9 1.357(3) . ?
N12 C13 1.406(2) . ?
N10 C9 1.318(2) . ?
C7 C1 1.465(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.397(3) . ?
C14 C15 1.376(3) . ?
C14 C13 1.387(3) . ?
C13 C18 1.381(3) . ?
C6 C5 1.388(3) . ?
C2 C3 1.375(3) . ?
C5 C4 1.367(3) . ?
C15 C16 1.375(3) . ?
C18 C17 1.384(3) . ?
C16 C17 1.369(3) . ?
C3 C4 1.375(3) . ?
_cod_duplicate_entry 1557711
