#------------------------------------------------------------------------------
#$Date: 2021-09-24 02:09:55 +0300 (Fri, 24 Sep 2021) $
#$Revision: 269272 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/83/7708393.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_7708393
loop_
_publ_author_name
'Mahanta, Sanjeev Pran'
'Choudhury, Diganta'
'Das, Rituraj'
'Talukdar, Dhrubajyoti'
'Sarma, Plaban Jyoti'
'Kuilya, Hemrupa'
'Thakuria, Ranjit'
_publ_section_title
;
 Colorimetric detection of fluoride ion in aqueous medium by thiourea
 derivatives: a transition metal ion assisted approach
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT02173G
_journal_year                    2021
_chemical_formula_sum            'C14 H12 N2 O2 S'
_chemical_formula_weight         272.32
_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   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-02-25 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.224(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2027(10)
_cell_length_b                   7.3419(6)
_cell_length_c                   15.7431(13)
_cell_measurement_reflns_used    6033
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.04
_cell_measurement_theta_min      3.61
_cell_volume                     1305.66(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17381
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         1.803
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Tetrahydrofuran'
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2284
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0344
_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)+(0.0532P)²+0.3696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2014
_reflns_number_total             2284
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt02173g2.cif
_cod_data_source_block           rt_ps45_spm_c3_0m_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7708393
_shelx_shelxl_version_number     2016/6
_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   0.939
_shelx_estimated_absorpt_t_max   0.971
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
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
C1 C 0.63639(13) 0.6401(2) 0.57208(10) 0.0366(4) Uani 1 1 d . . . . .
C2 C 0.68535(16) 0.5371(2) 0.65138(11) 0.0454(4) Uani 1 1 d . . . . .
H2 H 0.749945 0.462047 0.659492 0.055 Uiso 1 1 calc R U . . .
C3 C 0.63782(18) 0.5461(3) 0.71859(12) 0.0545(5) Uani 1 1 d . . . . .
H3 H 0.670739 0.477208 0.771824 0.065 Uiso 1 1 calc R U . . .
C4 C 0.54234(17) 0.6565(3) 0.70673(13) 0.0581(5) Uani 1 1 d . . . . .
H4 H 0.510535 0.661835 0.751838 0.070 Uiso 1 1 calc R U . . .
C5 C 0.49359(16) 0.7592(3) 0.62822(14) 0.0555(5) Uani 1 1 d . . . . .
H5 H 0.428859 0.833698 0.620421 0.067 Uiso 1 1 calc R U . . .
C6 C 0.54044(15) 0.7521(2) 0.56094(12) 0.0452(4) Uani 1 1 d . . . . .
H6 H 0.507626 0.822389 0.508199 0.054 Uiso 1 1 calc R U . . .
C7 C 0.68431(14) 0.6428(2) 0.49764(10) 0.0382(4) Uani 1 1 d . . . . .
C8 C 0.79700(13) 0.4536(2) 0.42780(10) 0.0372(4) Uani 1 1 d . . . . .
C9 C 0.83066(13) 0.5760(2) 0.29451(10) 0.0369(4) Uani 1 1 d . . . . .
C10 C 0.76818(13) 0.4750(2) 0.21780(10) 0.0340(3) Uani 1 1 d . . . . .
H10 H 0.703445 0.405578 0.215697 0.041 Uiso 1 1 calc R U . . .
C11 C 0.80326(12) 0.4782(2) 0.14372(9) 0.0324(3) Uani 1 1 d . . . . .
C12 C 0.89822(13) 0.5837(2) 0.14630(10) 0.0377(4) Uani 1 1 d . . . . .
H12 H 0.920449 0.587631 0.095970 0.045 Uiso 1 1 calc R U . . .
C13 C 0.95955(15) 0.6826(3) 0.22387(12) 0.0493(4) Uani 1 1 d . . . . .
H13 H 1.023944 0.752830 0.225915 0.059 Uiso 1 1 calc R U . . .
C14 C 0.92688(15) 0.6794(3) 0.29900(11) 0.0492(4) Uani 1 1 d . . . . .
H14 H 0.969113 0.745776 0.351541 0.059 Uiso 1 1 calc R U . . .
N1 N 0.74867(12) 0.4922(2) 0.49273(9) 0.0390(3) Uani 1 1 d . . . . .
N2 N 0.79016(14) 0.5856(2) 0.36894(9) 0.0430(3) Uani 1 1 d . . . . .
O1 O 0.66664(13) 0.77036(17) 0.44448(9) 0.0577(4) Uani 1 1 d . . . . .
O2 O 0.73953(11) 0.37581(16) 0.06855(7) 0.0471(3) Uani 1 1 d D . . . .
S1 S 0.85796(5) 0.24887(6) 0.42797(3) 0.05437(19) Uani 1 1 d . . . . .
H2A H 0.774(2) 0.387(4) 0.0221(14) 0.105(9) Uiso 1 1 d D . . . .
H1A H 0.7504(15) 0.403(3) 0.5268(12) 0.039(5) Uiso 1 1 d . . . . .
H2B H 0.7574(19) 0.683(3) 0.3738(15) 0.062(6) 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'
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
C6 C1 C2 119.53(14) . . ?
C6 C1 C7 117.06(15) . . ?
C2 C1 C7 123.38(14) . . ?
C1 C2 C3 119.90(17) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.18(18) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.13(16) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.27(17) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.99(17) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O1 C7 N1 122.36(14) . . ?
O1 C7 C1 121.90(14) . . ?
N1 C7 C1 115.73(14) . . ?
N2 C8 N1 115.77(14) . . ?
N2 C8 S1 124.67(12) . . ?
N1 C8 S1 119.56(12) . . ?
C10 C9 C14 121.38(14) . . ?
C10 C9 N2 119.70(14) . . ?
C14 C9 N2 118.76(14) . . ?
C9 C10 C11 118.96(13) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
O2 C11 C12 121.94(13) . . ?
O2 C11 C10 117.56(13) . . ?
C12 C11 C10 120.49(13) . . ?
C13 C12 C11 119.43(14) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.95(15) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C9 C14 C13 118.77(15) . . ?
C9 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C7 N1 C8 128.01(14) . . ?
C7 N1 H1A 117.7(12) . . ?
C8 N1 H1A 113.4(12) . . ?
C8 N2 C9 125.91(15) . . ?
C8 N2 H2B 118.0(15) . . ?
C9 N2 H2B 116.0(15) . . ?
C11 O2 H2A 109.7(16) . . ?
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
C1 C6 1.386(2) . ?
C1 C2 1.387(2) . ?
C1 C7 1.495(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.2195(19) . ?
C7 N1 1.375(2) . ?
C8 N2 1.322(2) . ?
C8 N1 1.3888(19) . ?
C8 S1 1.6767(17) . ?
C9 C10 1.376(2) . ?
C9 C14 1.377(2) . ?
C9 N2 1.4353(19) . ?
C10 C11 1.386(2) . ?
C10 H10 0.9300 . ?
C11 O2 1.3690(18) . ?
C11 C12 1.381(2) . ?
C12 C13 1.374(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
N1 H1A 0.840(19) . ?
N2 H2B 0.84(2) . ?
O2 H2A 0.972(10) . ?
