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#$Date: 2023-03-01 12:11:56 +0200 (Wed, 01 Mar 2023) $
#$Revision: 281212 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106798.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_8106798
loop_
_publ_author_name
'Wang, Xiao-Juan'
_publ_section_title
;
 Crystal structure of
 (R)-1-(1-(6-fluorobenzo[d]thiazol-2-yl)ethyl)-3-phenylthiourea
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              105
_journal_page_last               107
_journal_paper_doi               10.1515/ncrs-2015-0052
_journal_volume                  231
_journal_year                    2016
_chemical_absolute_configuration S
_chemical_formula_moiety         'C16 H14 F N3 S2'
_chemical_formula_sum            'C16 H14 F N3 S2'
_chemical_formula_weight         331.42
_chemical_name_common
(R)-1-(1-(6-fluorobenzo[d]thiazol-2-yl)ethyl)-3-phenylthiourea
_chemical_name_systematic
; 
 (R)-1-(1-(6-fluorobenzo[d]thiazol-2-yl)ethyl)-3-phenylthiourea 
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.443(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1583(9)
_cell_length_b                   28.524(4)
_cell_length_c                   7.6021(8)
_cell_measurement_temperature    293(2)
_cell_volume                     1547.6(3)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11985
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.2000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6179
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0547
_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)+(0.0343P)²+1.7506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1346
_reflns_number_gt                4911
_reflns_number_total             6179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0052_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P21
_cod_original_formula_sum        'C16 H14 F1 N3 S2'
_cod_database_code               8106798
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.2654(2) 0.66264(5) 0.33252(18) 0.0488(3) Uani 1 1 d . . .
S5 S 0.24877(17) 0.78818(4) 0.38253(18) 0.0436(3) Uani 1 1 d . . .
F1 F 0.6051(4) 0.93463(12) 0.6276(4) 0.0639(9) Uani 1 1 d . . .
N2 N -0.0448(5) 0.72686(14) 0.1984(5) 0.0391(10) Uani 1 1 d . . .
H2A H 0.0502 0.7337 0.1406 0.047 Uiso 1 1 calc R . .
N1 N -0.0378(6) 0.84389(14) 0.3810(5) 0.0396(10) Uani 1 1 d . . .
C14 C 0.0952(7) 0.66276(18) -0.0453(6) 0.0391(11) Uani 1 1 d . . .
C24 C 0.1196(7) 0.86984(16) 0.4401(6) 0.0369(11) Uani 1 1 d . . .
C26 C -0.1073(7) 0.68222(16) 0.1942(6) 0.0347(11) Uani 1 1 d . . .
C28 C 0.0473(8) 0.65916(19) -0.2253(7) 0.0478(13) Uani 1 1 d . . .
H28A H -0.0748 0.6517 -0.2664 0.057 Uiso 1 1 calc R . .
C30 C -0.1312(7) 0.76406(17) 0.2966(6) 0.0371(11) Uani 1 1 d . . .
H30A H -0.1704 0.7501 0.4057 0.044 Uiso 1 1 calc R . .
C38 C 0.2888(7) 0.84549(16) 0.4513(6) 0.0359(11) Uani 1 1 d . . .
C44 C 0.4569(7) 0.86674(18) 0.5147(7) 0.0447(12) Uani 1 1 d . . .
H44A H 0.5702 0.8506 0.5234 0.054 Uiso 1 1 calc R . .
C51 C 0.2819(7) 0.93817(18) 0.5523(7) 0.0443(12) Uani 1 1 d . . .
H51A H 0.2825 0.9694 0.5872 0.053 Uiso 1 1 calc R . .
C52 C 0.4440(7) 0.91294(19) 0.5631(7) 0.0415(12) Uani 1 1 d . . .
C58 C 0.2784(7) 0.6740(2) 0.0146(7) 0.0510(14) Uani 1 1 d . . .
H58A H 0.3111 0.6765 0.1350 0.061 Uiso 1 1 calc R . .
C60 C 0.0104(7) 0.80129(16) 0.3483(6) 0.0356(11) Uani 1 1 d . . .
C64 C 0.1178(8) 0.91709(18) 0.4895(7) 0.0499(14) Uani 1 1 d . . .
H64A H 0.0064 0.9340 0.4799 0.060 Uiso 1 1 calc R . .
C69 C 0.1818(9) 0.6667(2) -0.3432(7) 0.0565(15) Uani 1 1 d . . .
H69A H 0.1502 0.6641 -0.4638 0.068 Uiso 1 1 calc R . .
C70 C 0.4113(8) 0.6813(2) -0.1045(8) 0.0552(15) Uani 1 1 d . . .
H70A H 0.5340 0.6884 -0.0639 0.066 Uiso 1 1 calc R . .
C71 C -0.3050(7) 0.7834(2) 0.1958(8) 0.0544(14) Uani 1 1 d . . .
H71A H -0.3912 0.7583 0.1669 0.082 Uiso 1 1 calc R . .
H71B H -0.2709 0.7981 0.0893 0.082 Uiso 1 1 calc R . .
H71C H -0.3630 0.8060 0.2673 0.082 Uiso 1 1 calc R . .
C80 C 0.3634(9) 0.6783(2) -0.2828(9) 0.0593(17) Uani 1 1 d . . .
H80A H 0.4529 0.6840 -0.3626 0.071 Uiso 1 1 calc R . .
S2 S 0.25013(18) 1.05365(5) 1.08348(17) 0.0439(3) Uani 1 1 d . . .
S7 S 0.11393(17) 0.93626(4) 0.99746(18) 0.0440(3) Uani 1 1 d . . .
N4 N 0.4049(5) 0.88205(13) 1.0027(5) 0.0380(9) Uani 1 1 d . . .
F2 F -0.2253(5) 0.78915(13) 0.7356(5) 0.0720(10) Uani 1 1 d . . .
N5 N 0.5119(5) 0.99651(13) 0.9743(5) 0.0350(9) Uani 1 1 d . . .
H5A H 0.5943 0.9904 0.9010 0.042 Uiso 1 1 calc R . .
C18 C 0.2529(7) 0.85563(16) 0.9359(6) 0.0378(11) Uani 1 1 d . . .
C20 C 0.4851(6) 0.96176(16) 1.1118(6) 0.0331(10) Uani 1 1 d . . .
H20A H 0.4308 0.9773 1.2108 0.040 Uiso 1 1 calc R . .
C27 C 0.4183(6) 1.03717(15) 0.9532(6) 0.0322(10) Uani 1 1 d . . .
C33 C 0.0972(8) 0.7873(2) 0.8148(7) 0.0504(13) Uani 1 1 d . . .
H33A H 0.0994 0.7562 0.7785 0.060 Uiso 1 1 calc R . .
C35 C 0.6107(6) 1.05647(17) 0.7049(6) 0.0358(10) Uani 1 1 d . . .
C41 C 0.6745(6) 0.94134(19) 1.1760(7) 0.0428(12) Uani 1 1 d . . .
H41A H 0.7559 0.9661 1.2206 0.064 Uiso 1 1 calc R . .
H41B H 0.7289 0.9260 1.0797 0.064 Uiso 1 1 calc R . .
H41C H 0.6584 0.9190 1.2681 0.064 Uiso 1 1 calc R . .
C46 C 0.0793(7) 0.87923(17) 0.9227(6) 0.0377(11) Uani 1 1 d . . .
C49 C 0.9305(8) 1.0424(2) 0.6521(8) 0.0519(15) Uani 1 1 d . . .
H49A H 1.0531 1.0360 0.6949 0.062 Uiso 1 1 calc R . .
C53 C 0.7057(8) 1.0543(2) 0.4094(7) 0.0510(13) Uani 1 1 d . . .
H53A H 0.6761 1.0566 0.2884 0.061 Uiso 1 1 calc R . .
C55 C 0.2595(8) 0.80907(18) 0.8805(7) 0.0493(14) Uani 1 1 d . . .
H55A H 0.3726 0.7929 0.8878 0.059 Uiso 1 1 calc R . .
C57 C 0.7945(7) 1.04881(19) 0.7694(7) 0.0434(12) Uani 1 1 d . . .
H57A H 0.8260 1.0480 0.8904 0.052 Uiso 1 1 calc R . .
C61 C 0.3528(6) 0.92373(17) 1.0409(6) 0.0332(11) Uani 1 1 d . . .
C62 C 0.5671(7) 1.05994(18) 0.5236(6) 0.0438(12) Uani 1 1 d . . .
H62A H 0.4447 1.0661 0.4797 0.053 Uiso 1 1 calc R . .
C63 C -0.0660(8) 0.8116(2) 0.8036(7) 0.0493(14) Uani 1 1 d . . .
C74 C -0.0852(8) 0.8574(2) 0.8572(7) 0.0518(14) Uani 1 1 d . . .
H74A H -0.2004 0.8727 0.8500 0.062 Uiso 1 1 calc R . .
C78 C 0.8868(9) 1.0453(2) 0.4724(8) 0.0565(16) Uani 1 1 d . . .
H78A H 0.9795 1.0412 0.3946 0.068 Uiso 1 1 calc R . .
N3 N -0.0419(6) 0.65293(14) 0.0756(5) 0.0433(10) Uani 1 1 d . . .
H3A H -0.0880 0.6251 0.0721 0.052 Uiso 1 1 calc R . .
N6 N 0.4654(6) 1.06468(14) 0.8195(5) 0.0423(10) Uani 1 1 d . . .
H6A H 0.4009 1.0899 0.8013 0.051 Uiso 1 1 calc R . .
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'
S S 0.1246 0.1234 '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'
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
C38 S5 C60 88.8(2) . .
C26 N2 C30 123.0(4) . .
C26 N2 H2A 118.5 . .
C30 N2 H2A 118.5 . .
C60 N1 C24 109.9(4) . .
C28 C14 C58 119.6(5) . .
C28 C14 N3 119.5(5) . .
C58 C14 N3 120.9(5) . .
C38 C24 N1 115.6(4) . .
C38 C24 C64 119.4(5) . .
N1 C24 C64 125.0(5) . .
N3 C26 N2 118.1(4) . .
N3 C26 S1 119.7(4) . .
N2 C26 S1 122.1(4) . .
C69 C28 C14 119.7(5) . .
C69 C28 H28A 120.1 . .
C14 C28 H28A 120.1 . .
N2 C30 C60 110.1(4) . .
N2 C30 C71 111.7(4) . .
C60 C30 C71 112.8(4) . .
N2 C30 H30A 107.3 . .
C60 C30 H30A 107.3 . .
C71 C30 H30A 107.3 . .
C24 C38 C44 121.7(4) . .
C24 C38 S5 109.2(3) . .
C44 C38 S5 129.0(4) . .
C52 C44 C38 115.7(5) . .
C52 C44 H44A 122.1 . .
C38 C44 H44A 122.1 . .
C52 C51 C64 119.5(5) . .
C52 C51 H51A 120.3 . .
C64 C51 H51A 120.3 . .
C51 C52 F1 118.3(5) . .
C51 C52 C44 124.4(5) . .
F1 C52 C44 117.3(5) . .
C70 C58 C14 120.0(5) . .
C70 C58 H58A 120.0 . .
C14 C58 H58A 120.0 . .
N1 C60 C30 122.1(4) . .
N1 C60 S5 116.4(4) . .
C30 C60 S5 121.3(4) . .
C51 C64 C24 119.3(5) . .
C51 C64 H64A 120.3 . .
C24 C64 H64A 120.3 . .
C28 C69 C80 120.3(5) . .
C28 C69 H69A 119.8 . .
C80 C69 H69A 119.8 . .
C80 C70 C58 120.3(6) . .
C80 C70 H70A 119.8 . .
C58 C70 H70A 119.8 . .
C30 C71 H71A 109.5 . .
C30 C71 H71B 109.5 . .
H71A C71 H71B 109.5 . .
C30 C71 H71C 109.5 . .
H71A C71 H71C 109.5 . .
H71B C71 H71C 109.5 . .
C70 C80 C69 119.9(6) . .
C70 C80 H80A 120.1 . .
C69 C80 H80A 120.1 . .
C46 S7 C61 89.0(2) . .
C61 N4 C18 110.6(4) . .
C27 N5 C20 125.3(4) . .
C27 N5 H5A 117.3 . .
C20 N5 H5A 117.3 . .
N4 C18 C55 125.7(5) . .
N4 C18 C46 115.4(4) . .
C55 C18 C46 118.9(5) . .
N5 C20 C61 110.2(4) . .
N5 C20 C41 109.0(4) . .
C61 C20 C41 111.0(4) . .
N5 C20 H20A 108.9 . .
C61 C20 H20A 108.9 . .
C41 C20 H20A 108.9 . .
N5 C27 N6 116.2(4) . .
N5 C27 S2 122.9(4) . .
N6 C27 S2 120.9(4) . .
C63 C33 C55 119.5(5) . .
C63 C33 H33A 120.3 . .
C55 C33 H33A 120.3 . .
C57 C35 C62 119.7(5) . .
C57 C35 N6 121.8(4) . .
C62 C35 N6 118.3(4) . .
C20 C41 H41A 109.5 . .
C20 C41 H41B 109.5 . .
H41A C41 H41B 109.5 . .
C20 C41 H41C 109.5 . .
H41A C41 H41C 109.5 . .
H41B C41 H41C 109.5 . .
C74 C46 C18 122.0(5) . .
C74 C46 S7 129.3(4) . .
C18 C46 S7 108.8(4) . .
C78 C49 C57 120.9(5) . .
C78 C49 H49A 119.6 . .
C57 C49 H49A 119.6 . .
C78 C53 C62 120.6(5) . .
C78 C53 H53A 119.7 . .
C62 C53 H53A 119.7 . .
C33 C55 C18 119.4(5) . .
C33 C55 H55A 120.3 . .
C18 C55 H55A 120.3 . .
C49 C57 C35 119.3(5) . .
C49 C57 H57A 120.3 . .
C35 C57 H57A 120.3 . .
N4 C61 C20 124.0(4) . .
N4 C61 S7 116.2(4) . .
C20 C61 S7 119.7(3) . .
C53 C62 C35 119.9(5) . .
C53 C62 H62A 120.1 . .
C35 C62 H62A 120.1 . .
C33 C63 F2 118.1(5) . .
C33 C63 C74 124.8(5) . .
F2 C63 C74 117.0(5) . .
C63 C74 C46 115.4(5) . .
C63 C74 H74A 122.3 . .
C46 C74 H74A 122.3 . .
C53 C78 C49 119.5(5) . .
C53 C78 H78A 120.2 . .
C49 C78 H78A 120.2 . .
C26 N3 C14 127.3(4) . .
C26 N3 H3A 116.4 . .
C14 N3 H3A 116.4 . .
C27 N6 C35 127.0(4) . .
C27 N6 H6A 116.5 . .
C35 N6 H6A 116.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C26 1.698(5) .
S5 C38 1.733(5) .
S5 C60 1.747(5) .
F1 C52 1.365(6) .
N2 C26 1.349(6) .
N2 C30 1.462(6) .
N2 H2A 0.8600 .
N1 C60 1.292(6) .
N1 C24 1.393(6) .
C14 C28 1.388(7) .
C14 C58 1.392(7) .
C14 N3 1.424(6) .
C24 C38 1.393(7) .
C24 C64 1.399(7) .
C26 N3 1.340(6) .
C28 C69 1.382(8) .
C28 H28A 0.9300 .
C30 C60 1.499(6) .
C30 C71 1.513(7) .
C30 H30A 0.9800 .
C38 C44 1.400(7) .
C44 C52 1.373(7) .
C44 H44A 0.9300 .
C51 C52 1.363(7) .
C51 C64 1.372(7) .
C51 H51A 0.9300 .
C58 C70 1.380(8) .
C58 H58A 0.9300 .
C64 H64A 0.9300 .
C69 C80 1.385(8) .
C69 H69A 0.9300 .
C70 C80 1.375(9) .
C70 H70A 0.9300 .
C71 H71A 0.9600 .
C71 H71B 0.9600 .
C71 H71C 0.9600 .
C80 H80A 0.9300 .
S2 C27 1.684(5) .
S7 C46 1.735(5) .
S7 C61 1.753(5) .
N4 C61 1.286(6) .
N4 C18 1.387(6) .
F2 C63 1.373(6) .
N5 C27 1.343(5) .
N5 C20 1.464(6) .
N5 H5A 0.8600 .
C18 C55 1.395(7) .
C18 C46 1.410(7) .
C20 C61 1.512(6) .
C20 C41 1.521(6) .
C20 H20A 0.9800 .
C27 N6 1.348(6) .
C33 C63 1.355(8) .
C33 C55 1.377(7) .
C33 H33A 0.9300 .
C35 C57 1.385(7) .
C35 C62 1.393(6) .
C35 N6 1.427(6) .
C41 H41A 0.9600 .
C41 H41B 0.9600 .
C41 H41C 0.9600 .
C46 C74 1.390(7) .
C49 C78 1.381(8) .
C49 C57 1.383(7) .
C49 H49A 0.9300 .
C53 C78 1.371(8) .
C53 C62 1.377(7) .
C53 H53A 0.9300 .
C55 H55A 0.9300 .
C57 H57A 0.9300 .
C62 H62A 0.9300 .
C63 C74 1.378(8) .
C74 H74A 0.9300 .
C78 H78A 0.9300 .
N3 H3A 0.8600 .
N6 H6A 0.8600 .
