#------------------------------------------------------------------------------
#$Date: 2023-10-18 01:53:53 +0300 (Wed, 18 Oct 2023) $
#$Revision: 287008 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/42/7714233.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_7714233
loop_
_publ_author_name
'Benny, Renitta'
'De, Soumen'
_publ_section_title
;
 Interplay between anti-anti and syn-anti conformation of thiourea
 modulating ON-OFF catalysis
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT02398B
_journal_year                    2023
_chemical_formula_moiety         'C19 H18 F6 N2 S'
_chemical_formula_sum            'C19 H18 F6 N2 S'
_chemical_formula_weight         420.41
_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-2018/3
_audit_update_record
;
2023-09-24 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.956(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3638(13)
_cell_length_b                   28.079(4)
_cell_length_c                   8.3943(13)
_cell_measurement_reflns_used    7154
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.51
_cell_volume                     1913.2(5)
_computing_cell_refinement       'APEX3/SAINT (Br uker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      140(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker KAPPA 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  0.0546
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            42523
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.509
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      1.460
_exptl_crystal_density_method    NONE
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.068
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3345
_refine_ls_number_restraints     126
_refine_ls_restrained_S_all      1.223
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0154P)²+2.1782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0949
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2740
_reflns_number_total             3345
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt02398b2.cif
_cod_data_source_block           shelx_CCDC1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7714233
_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   0.984
_shelx_estimated_absorpt_t_max   0.992
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 0.4370(3) 0.42477(8) 0.8680(3) 0.0229(5) Uani 1 1 d . . . . .
C2 C 0.6302(3) 0.44815(7) 0.6996(3) 0.0234(5) Uani 1 1 d . . . . .
C3 C 0.7990(3) 0.45363(8) 0.7479(3) 0.0246(5) Uani 1 1 d . . . . .
H3 H 0.849262 0.464377 0.855621 0.030 Uiso 1 1 calc R U . . .
C4 C 0.8948(3) 0.44342(8) 0.6387(3) 0.0245(5) Uani 1 1 d . . . . .
H4 H 1.010768 0.447669 0.672769 0.029 Uiso 1 1 calc R U . . .
C5 C 0.8260(3) 0.42710(7) 0.4805(3) 0.0221(5) Uani 1 1 d . . . . .
C6 C 0.6548(3) 0.42341(8) 0.4329(3) 0.0281(5) Uani 1 1 d . . . . .
H6 H 0.603705 0.413273 0.324651 0.034 Uiso 1 1 calc R U . . .
C7 C 0.5581(3) 0.43421(9) 0.5402(3) 0.0291(5) Uani 1 1 d . . . . .
H7 H 0.441597 0.432061 0.504510 0.035 Uiso 1 1 calc R U . . .
C8 C 0.9291(3) 0.41151(8) 0.3619(3) 0.0256(5) Uani 1 1 d . . . . .
C9 C 0.9118(3) 0.35731(9) 0.3394(3) 0.0395(6) Uani 1 1 d . . . . .
H9A H 0.979237 0.346492 0.265776 0.059 Uiso 1 1 calc R U . . .
H9B H 0.796120 0.349245 0.291832 0.059 Uiso 1 1 calc R U . . .
H9C H 0.949017 0.341609 0.446197 0.059 Uiso 1 1 calc R U . . .
C10 C 0.8683(3) 0.43590(10) 0.1950(3) 0.0351(6) Uani 1 1 d . . . . .
H10A H 0.874247 0.470534 0.209680 0.053 Uiso 1 1 calc R U . . .
H10B H 0.754078 0.426513 0.146721 0.053 Uiso 1 1 calc R U . . .
H10C H 0.937879 0.426254 0.121912 0.053 Uiso 1 1 calc R U . . .
C11 C 1.1119(3) 0.42321(10) 0.4266(3) 0.0339(6) Uani 1 1 d . . . . .
H11A H 1.125092 0.457555 0.446092 0.051 Uiso 1 1 calc R U . . .
H11B H 1.172434 0.413491 0.345552 0.051 Uiso 1 1 calc R U . . .
H11C H 1.155229 0.406065 0.529704 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3493(3) 0.33932(8) 0.8305(3) 0.0223(5) Uani 1 1 d . . . . .
C13 C 0.4279(3) 0.29558(8) 0.8364(3) 0.0244(5) Uani 1 1 d . . . . .
H13 H 0.539359 0.294129 0.828980 0.029 Uiso 1 1 calc R U . . .
C14 C 0.3440(3) 0.25395(8) 0.8533(3) 0.0255(5) Uani 1 1 d . . . . .
C15 C 0.1825(3) 0.25543(8) 0.8654(3) 0.0266(5) Uani 1 1 d . . . . .
H15 H 0.125702 0.226958 0.878611 0.032 Uiso 1 1 calc R U . . .
C16 C 0.1046(3) 0.29933(8) 0.8580(3) 0.0245(5) Uani 1 1 d . . . . .
C17 C 0.1858(3) 0.34126(8) 0.8393(3) 0.0237(5) Uani 1 1 d . . . . .
H17 H 0.130128 0.370961 0.832498 0.028 Uiso 1 1 calc R U . . .
C18 C -0.0721(3) 0.30077(9) 0.8653(3) 0.0354(6) Uani 1 1 d . . . . .
C19 C 0.4311(3) 0.20704(9) 0.8589(3) 0.0348(6) Uani 1 1 d . . . . .
N1 N 0.5312(2) 0.45699(6) 0.8139(2) 0.0262(4) Uani 1 1 d . . . . .
H1 H 0.531868 0.486165 0.852385 0.031 Uiso 1 1 calc R U . . .
N2 N 0.4384(2) 0.38019(6) 0.8039(2) 0.0261(4) Uani 1 1 d . . . . .
H2 H 0.503666 0.376317 0.736866 0.031 Uiso 1 1 calc R U . . .
S1 S 0.33112(7) 0.43937(2) 1.00753(7) 0.02721(16) Uani 1 1 d . . . . .
F1 F 0.3550(5) 0.17229(11) 0.9197(9) 0.089(2) Uani 0.654(6) 1 d D U P A 1
F2 F 0.5774(5) 0.20779(14) 0.9734(6) 0.0761(15) Uani 0.654(6) 1 d D U P A 1
F3 F 0.4639(9) 0.1946(2) 0.7284(5) 0.102(3) Uani 0.654(6) 1 d D U P A 1
F4 F -0.1336(6) 0.34294(13) 0.8686(10) 0.092(2) Uani 0.654(6) 1 d D U P A 1
F5 F -0.0921(5) 0.27961(18) 1.0051(5) 0.0691(13) Uani 0.654(6) 1 d D U P A 1
F6 F -0.1669(4) 0.2754(2) 0.7531(6) 0.0834(18) Uani 0.654(6) 1 d D U P A 1
F1' F 0.4899(14) 0.1903(3) 0.9895(7) 0.072(3) Uani 0.346(6) 1 d D U P A 2
F2' F 0.5434(11) 0.2082(3) 0.7724(13) 0.069(3) Uani 0.346(6) 1 d D U P A 2
F3' F 0.3260(6) 0.17385(19) 0.7654(12) 0.059(2) Uani 0.346(6) 1 d D U P A 2
F4' F -0.1321(9) 0.2641(2) 0.9033(18) 0.086(3) Uani 0.346(6) 1 d D U P A 2
F5' F -0.1039(11) 0.3350(3) 0.9522(12) 0.078(3) Uani 0.346(6) 1 d D U P A 2
F6' F -0.1696(8) 0.3137(5) 0.7153(8) 0.088(3) Uani 0.346(6) 1 d D U P A 2
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'
F F 0.0171 0.0103 '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'
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
N1 C1 N2 114.94(19) . . ?
N1 C1 S1 121.33(17) . . ?
N2 C1 S1 123.71(17) . . ?
C3 C2 C7 119.4(2) . . ?
C3 C2 N1 120.0(2) . . ?
C7 C2 N1 120.6(2) . . ?
C2 C3 C4 119.8(2) . . ?
C3 C4 C5 121.8(2) . . ?
C4 C5 C6 117.3(2) . . ?
C4 C5 C8 123.1(2) . . ?
C6 C5 C8 119.6(2) . . ?
C7 C6 C5 121.3(2) . . ?
C6 C7 C2 120.3(2) . . ?
C5 C8 C11 112.30(19) . . ?
C5 C8 C10 110.65(19) . . ?
C11 C8 C10 108.14(19) . . ?
C5 C8 C9 108.21(19) . . ?
C11 C8 C9 108.2(2) . . ?
C10 C8 C9 109.3(2) . . ?
C13 C12 C17 119.8(2) . . ?
C13 C12 N2 117.4(2) . . ?
C17 C12 N2 122.6(2) . . ?
C14 C13 C12 120.1(2) . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 C19 120.0(2) . . ?
C13 C14 C19 119.3(2) . . ?
C14 C15 C16 118.7(2) . . ?
C17 C16 C15 121.4(2) . . ?
C17 C16 C18 119.9(2) . . ?
C15 C16 C18 118.7(2) . . ?
C16 C17 C12 119.2(2) . . ?
F4' C18 F5' 109.4(6) . . ?
F4 C18 F6 110.1(4) . . ?
F4 C18 F5 104.4(4) . . ?
F6 C18 F5 101.9(3) . . ?
F4' C18 F6' 105.8(6) . . ?
F5' C18 F6' 99.5(5) . . ?
F4' C18 C16 117.4(4) . . ?
F5' C18 C16 112.9(5) . . ?
F4 C18 C16 115.3(3) . . ?
F6 C18 C16 113.3(2) . . ?
F5 C18 C16 110.6(3) . . ?
F6' C18 C16 110.2(3) . . ?
F1' C19 F2' 109.1(6) . . ?
F3 C19 F1 111.0(4) . . ?
F3 C19 F2 105.9(4) . . ?
F1 C19 F2 99.9(3) . . ?
F1' C19 F3' 108.8(5) . . ?
F2' C19 F3' 98.2(5) . . ?
F1' C19 C14 117.9(4) . . ?
F3 C19 C14 115.4(3) . . ?
F2' C19 C14 111.4(4) . . ?
F1 C19 C14 112.5(2) . . ?
F2 C19 C14 110.8(2) . . ?
F3' C19 C14 109.6(3) . . ?
C1 N1 C2 126.04(18) . . ?
C1 N2 C12 128.86(19) . . ?
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 N1 1.348(3) . ?
C1 N2 1.364(3) . ?
C1 S1 1.681(2) . ?
C2 C3 1.380(3) . ?
C2 C7 1.385(3) . ?
C2 N1 1.432(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.391(3) . ?
C5 C6 1.394(3) . ?
C5 C8 1.530(3) . ?
C6 C7 1.382(3) . ?
C8 C11 1.530(3) . ?
C8 C10 1.532(3) . ?
C8 C9 1.536(3) . ?
C12 C13 1.388(3) . ?
C12 C17 1.389(3) . ?
C12 N2 1.415(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.380(3) . ?
C14 C19 1.500(3) . ?
C15 C16 1.389(3) . ?
C16 C17 1.387(3) . ?
C16 C18 1.494(3) . ?
C18 F4' 1.221(6) . ?
C18 F5' 1.274(7) . ?
C18 F4 1.294(4) . ?
C18 F6 1.289(4) . ?
C18 F5 1.361(4) . ?
C18 F6' 1.373(7) . ?
C19 F1' 1.186(6) . ?
C19 F3 1.242(5) . ?
C19 F2' 1.320(8) . ?
C19 F1 1.332(4) . ?
C19 F2 1.362(4) . ?
C19 F3' 1.387(5) . ?
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
C17 H17 S1 0.95 2.74 3.199(2) 110.8 . yes
N1 H1 S1 0.88 2.53 3.3478(19) 154.3 3_667 yes
C17 H17 S1 0.95 2.74 3.199(2) 110.8 . yes
N1 H1 S1 0.88 2.53 3.3478(19) 154.3 3_667 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
_geom_torsion_publ_flag
C7 C2 C3 C4 -2.5(3) . . . . ?
N1 C2 C3 C4 177.7(2) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 2.8(3) . . . . ?
C3 C4 C5 C8 -174.7(2) . . . . ?
C4 C5 C6 C7 -1.8(3) . . . . ?
C8 C5 C6 C7 175.8(2) . . . . ?
C5 C6 C7 C2 -1.3(4) . . . . ?
C3 C2 C7 C6 3.4(3) . . . . ?
N1 C2 C7 C6 -176.7(2) . . . . ?
C4 C5 C8 C11 -8.9(3) . . . . ?
C6 C5 C8 C11 173.6(2) . . . . ?
C4 C5 C8 C10 -129.9(2) . . . . ?
C6 C5 C8 C10 52.7(3) . . . . ?
C4 C5 C8 C9 110.4(2) . . . . ?
C6 C5 C8 C9 -67.0(3) . . . . ?
C17 C12 C13 C14 -0.8(3) . . . . ?
N2 C12 C13 C14 -176.5(2) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C12 C13 C14 C19 179.8(2) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C19 C14 C15 C16 -179.3(2) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C14 C15 C16 C18 177.9(2) . . . . ?
C15 C16 C17 C12 -1.1(3) . . . . ?
C18 C16 C17 C12 -179.1(2) . . . . ?
C13 C12 C17 C16 1.6(3) . . . . ?
N2 C12 C17 C16 177.0(2) . . . . ?
C17 C16 C18 F4' -170.6(8) . . . . ?
C15 C16 C18 F4' 11.3(9) . . . . ?
C17 C16 C18 F5' -42.0(7) . . . . ?
C15 C16 C18 F5' 140.0(6) . . . . ?
C17 C16 C18 F4 -6.3(5) . . . . ?
C15 C16 C18 F4 175.7(4) . . . . ?
C17 C16 C18 F6 121.9(5) . . . . ?
C15 C16 C18 F6 -56.2(5) . . . . ?
C17 C16 C18 F5 -124.4(3) . . . . ?
C15 C16 C18 F5 57.5(4) . . . . ?
C17 C16 C18 F6' 68.3(7) . . . . ?
C15 C16 C18 F6' -109.7(7) . . . . ?
C15 C14 C19 F1' -82.9(8) . . . . ?
C13 C14 C19 F1' 96.8(8) . . . . ?
C15 C14 C19 F3 111.6(5) . . . . ?
C13 C14 C19 F3 -68.7(5) . . . . ?
C15 C14 C19 F2' 149.9(5) . . . . ?
C13 C14 C19 F2' -30.4(6) . . . . ?
C15 C14 C19 F1 -17.1(5) . . . . ?
C13 C14 C19 F1 162.6(4) . . . . ?
C15 C14 C19 F2 -128.1(3) . . . . ?
C13 C14 C19 F2 51.7(4) . . . . ?
C15 C14 C19 F3' 42.3(6) . . . . ?
C13 C14 C19 F3' -138.0(5) . . . . ?
N2 C1 N1 C2 -0.6(3) . . . . ?
S1 C1 N1 C2 177.96(18) . . . . ?
C3 C2 N1 C1 -117.3(2) . . . . ?
C7 C2 N1 C1 62.9(3) . . . . ?
N1 C1 N2 C12 -177.5(2) . . . . ?
S1 C1 N2 C12 4.0(3) . . . . ?
C13 C12 N2 C1 -143.8(2) . . . . ?
C17 C12 N2 C1 40.6(4) . . . . ?
