#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/49/2214920.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2214920
loop_
_publ_author_name
'Tan, Zhi-Wei'
'Tan, Xiao-Hong'
'Song, Xin-Jian'
_publ_section_title
1-(3-Methylphenyl)-3-{5-[4-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}urea
_journal_coeditor_code           XU2300
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3641
_journal_page_last               o3641
_journal_paper_doi               10.1107/S1600536807036343
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C17 H13 F3 N4 O S'
_chemical_formula_moiety         'C17 H13 F3 N4 O S'
_chemical_formula_sum            'C17 H13 F3 N4 O S'
_chemical_formula_weight         378.38
_chemical_name_systematic
1-(3-Methylphenyl)-3-{5-[4-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}urea
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                99.972(3)
_cell_angle_beta                 92.435(4)
_cell_angle_gamma                94.290(3)
_cell_formula_units_Z            2
_cell_length_a                   5.4780(10)
_cell_length_b                   8.0133(14)
_cell_length_c                   19.351(3)
_cell_measurement_reflns_used    1187
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      22.1
_cell_measurement_theta_min      2.6
_cell_volume                     832.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_sigmaI/netI    0.057
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4221
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.321
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2889
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1058P)²+0.1695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1792
_refine_ls_wR_factor_ref         0.2039
_reflns_number_gt                2203
_reflns_number_total             2889
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2300.cif
_cod_data_source_block           I
_cod_database_code               2214920
_cod_database_fobs_code          2214920
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3164(11) 0.3797(7) -0.3256(2) 0.0919(18) Uani d . 1 . .
H H1A 0.4439 0.3032 -0.3295 0.138 Uiso calc R 1 . .
H H1B 0.3728 0.4827 -0.3411 0.138 Uiso calc R 1 . .
H H1C 0.1747 0.3273 -0.3544 0.138 Uiso calc R 1 . .
C C2 0.4087(7) 0.5277(5) -0.2014(2) 0.0517(10) Uani d . 1 . .
H H2 0.5538 0.5741 -0.2163 0.062 Uiso calc R 1 . .
C C3 0.2499(9) 0.4203(5) -0.2499(2) 0.0604(12) Uani d . 1 . .
C C4 0.0373(9) 0.3538(6) -0.2259(3) 0.0676(12) Uani d . 1 . .
H H4 -0.0733 0.2815 -0.2572 0.081 Uiso calc R 1 . .
C C5 -0.0134(8) 0.3925(5) -0.1569(2) 0.0642(11) Uani d . 1 . .
H H5 -0.1593 0.3465 -0.1423 0.077 Uiso calc R 1 . .
C C6 0.1433(7) 0.4969(5) -0.1082(2) 0.0503(9) Uani d . 1 . .
H H6 0.1076 0.5197 -0.0611 0.060 Uiso calc R 1 . .
C C7 0.3573(7) 0.5676(4) -0.13140(18) 0.0423(8) Uani d . 1 . .
C C8 0.5228(6) 0.7434(5) -0.01756(18) 0.0424(8) Uani d . 1 . .
C C9 0.7631(7) 0.9361(5) 0.07428(18) 0.0438(9) Uani d . 1 . .
C C10 0.7901(6) 1.0522(4) 0.19476(18) 0.0428(9) Uani d . 1 . .
C C11 0.7676(7) 1.1034(5) 0.27066(18) 0.0463(9) Uani d . 1 . .
C C12 0.5630(9) 1.0524(6) 0.3030(2) 0.0731(13) Uani d . 1 . .
H H12 0.4356 0.9858 0.2758 0.088 Uiso calc R 1 . .
C C13 0.5405(10) 1.0969(6) 0.3743(2) 0.0795(14) Uani d . 1 . .
H H13 0.3998 1.0615 0.3948 0.095 Uiso calc R 1 . .
C C14 0.7283(9) 1.1941(5) 0.4146(2) 0.0638(12) Uani d . 1 A .
C C15 0.9277(10) 1.2474(7) 0.3834(2) 0.0781(14) Uani d . 1 . .
H H15 1.0533 1.3154 0.4107 0.094 Uiso calc R 1 . .
C C16 0.9507(9) 1.2039(6) 0.3120(2) 0.0706(12) Uani d . 1 . .
H H16 1.0903 1.2428 0.2918 0.085 Uiso calc R 1 . .
C C17 0.7119(15) 1.2439(9) 0.4920(3) 0.096(2) Uani d . 1 . .
F F1 0.4700(19) 1.2214(17) 0.5122(9) 0.121(4) Uani d PD 0.67 A 1
F F2 0.829(2) 1.1386(11) 0.5265(4) 0.126(3) Uani d PD 0.67 A 1
F F3 0.788(3) 1.3979(13) 0.5189(5) 0.147(6) Uani d PD 0.67 A 1
F F1' 0.552(5) 1.180(4) 0.5166(18) 0.138(9) Uani d PDU 0.33 A 2
F F2' 0.907(4) 1.252(4) 0.5279(10) 0.181(12) Uani d PD 0.33 A 2
F F3' 0.672(5) 1.410(3) 0.5021(11) 0.163(12) Uani d PD 0.33 A 2
N N1 0.5294(5) 0.6798(4) -0.08729(15) 0.0476(8) Uani d . 1 . .
H H1 0.6555 0.7089 -0.1080 0.057 Uiso d R 1 . .
N N2 0.7195(5) 0.8563(4) 0.00599(14) 0.0492(8) Uani d . 1 . .
H H2A 0.8396 0.8756 -0.0201 0.059 Uiso d R 1 . .
N N3 0.9620(5) 1.0398(4) 0.09270(15) 0.0494(8) Uani d . 1 . .
N N4 0.9775(6) 1.1066(4) 0.16332(15) 0.0495(8) Uani d . 1 . .
O O1 0.3635(5) 0.7090(3) 0.02018(13) 0.0579(7) Uani d . 1 . .
S S1 0.57658(17) 0.91409(12) 0.14109(5) 0.0467(3) Uani d . 1 . .
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'
F F 0.0171 0.0103 '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
C3 C1 H1A 109.5
C3 C1 H1B 109.5
H1A C1 H1B 109.5
C3 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C7 C2 C3 121.7(4)
C7 C2 H2 119.2
C3 C2 H2 119.2
C4 C3 C2 117.5(4)
C4 C3 C1 123.0(4)
C2 C3 C1 119.5(5)
C5 C4 C3 120.9(4)
C5 C4 H4 119.5
C3 C4 H4 119.5
C4 C5 C6 122.2(4)
C4 C5 H5 118.9
C6 C5 H5 118.9
C5 C6 C7 117.9(4)
C5 C6 H6 121.0
C7 C6 H6 121.0
C2 C7 C6 119.8(4)
C2 C7 N1 116.8(3)
C6 C7 N1 123.5(3)
O1 C8 N1 125.8(3)
O1 C8 N2 122.5(3)
N1 C8 N2 111.7(3)
N3 C9 N2 120.0(3)
N3 C9 S1 114.8(3)
N2 C9 S1 125.2(3)
N4 C10 C11 121.7(3)
N4 C10 S1 115.1(3)
C11 C10 S1 123.2(3)
C16 C11 C12 117.6(4)
C16 C11 C10 121.0(4)
C12 C11 C10 121.4(4)
C11 C12 C13 122.2(5)
C11 C12 H12 118.9
C13 C12 H12 118.9
C14 C13 C12 119.1(5)
C14 C13 H13 120.5
C12 C13 H13 120.5
C15 C14 C13 119.3(4)
C15 C14 C17 120.0(5)
C13 C14 C17 120.7(5)
C14 C15 C16 121.9(5)
C14 C15 H15 119.0
C16 C15 H15 119.0
C11 C16 C15 119.9(4)
C11 C16 H16 120.0
C15 C16 H16 120.0
F1' C17 F2' 111.9(18)
F3 C17 F2 108.7(8)
F1' C17 F3' 105.1(14)
F2' C17 F3' 99.8(14)
F3 C17 F1 105.8(8)
F2 C17 F1 102.3(7)
F1' C17 C14 116.7(18)
F2' C17 C14 116.0(12)
F3 C17 C14 116.4(7)
F2 C17 C14 110.9(6)
F3' C17 C14 104.9(11)
F1 C17 C14 111.7(8)
C8 N1 C7 129.2(3)
C8 N1 H1 117.4
C7 N1 H1 113.4
C8 N2 C9 124.2(3)
C8 N2 H2A 122.7
C9 N2 H2A 112.7
C9 N3 N4 112.1(3)
C10 N4 N3 111.6(3)
C9 S1 C10 86.44(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C3 1.511(6)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C7 1.383(5)
C2 C3 1.385(6)
C2 H2 0.9300
C3 C4 1.377(7)
C4 C5 1.364(6)
C4 H4 0.9300
C5 C6 1.369(6)
C5 H5 0.9300
C6 C7 1.389(5)
C6 H6 0.9300
C7 N1 1.402(4)
C8 O1 1.208(4)
C8 N1 1.360(4)
C8 N2 1.363(4)
C9 N3 1.316(5)
C9 N2 1.367(5)
C9 S1 1.706(3)
C10 N4 1.300(5)
C10 C11 1.468(5)
C10 S1 1.726(4)
C11 C16 1.372(6)
C11 C12 1.376(6)
C12 C13 1.378(6)
C12 H12 0.9300
C13 C14 1.369(7)
C13 H13 0.9300
C14 C15 1.348(7)
C14 C17 1.490(7)
C15 C16 1.379(6)
C15 H15 0.9300
C16 H16 0.9300
C17 F1' 1.15(3)
C17 F2' 1.24(2)
C17 F3 1.284(12)
C17 F2 1.344(12)
C17 F3' 1.35(2)
C17 F1 1.405(14)
N1 H1 0.8513
N2 H2A 0.8663
N3 N4 1.375(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A N3 2_775 0.87 1.99 2.829(4) 162
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
C7 C2 C3 C4 -0.1(6)
C7 C2 C3 C1 -179.4(4)
C2 C3 C4 C5 -0.1(6)
C1 C3 C4 C5 179.2(4)
C3 C4 C5 C6 -0.6(7)
C4 C5 C6 C7 1.6(6)
C3 C2 C7 C6 1.1(5)
C3 C2 C7 N1 -179.0(3)
C5 C6 C7 C2 -1.8(5)
C5 C6 C7 N1 178.3(3)
N4 C10 C11 C16 -3.4(6)
S1 C10 C11 C16 175.3(3)
N4 C10 C11 C12 176.6(4)
S1 C10 C11 C12 -4.7(5)
C16 C11 C12 C13 -1.1(7)
C10 C11 C12 C13 178.9(4)
C11 C12 C13 C14 -0.4(8)
C12 C13 C14 C15 1.6(8)
C12 C13 C14 C17 -179.6(5)
C13 C14 C15 C16 -1.4(8)
C17 C14 C15 C16 179.8(5)
C12 C11 C16 C15 1.3(7)
C10 C11 C16 C15 -178.7(4)
C14 C15 C16 C11 -0.1(8)
C15 C14 C17 F1' -171.5(17)
C13 C14 C17 F1' 9.7(18)
C15 C14 C17 F2' -36(2)
C13 C14 C17 F2' 144.9(19)
C15 C14 C17 F3 40.9(12)
C13 C14 C17 F3 -137.9(10)
C15 C14 C17 F2 -84.0(8)
C13 C14 C17 F2 97.2(9)
C15 C14 C17 F3' 72.7(14)
C13 C14 C17 F3' -106.1(13)
C15 C14 C17 F1 162.5(7)
C13 C14 C17 F1 -16.3(10)
O1 C8 N1 C7 2.1(6)
N2 C8 N1 C7 -176.8(3)
C2 C7 N1 C8 178.2(3)
C6 C7 N1 C8 -1.9(6)
O1 C8 N2 C9 2.9(6)
N1 C8 N2 C9 -178.1(3)
N3 C9 N2 C8 178.1(3)
S1 C9 N2 C8 -2.1(5)
N2 C9 N3 N4 -179.2(3)
S1 C9 N3 N4 1.0(4)
C11 C10 N4 N3 178.8(3)
S1 C10 N4 N3 0.0(4)
C9 N3 N4 C10 -0.6(4)
N3 C9 S1 C10 -0.8(3)
N2 C9 S1 C10 179.4(3)
N4 C10 S1 C9 0.4(3)
C11 C10 S1 C9 -178.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139072835
