#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/59/2225974.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_2225974
loop_
_publ_author_name
'Saeed, Aamer'
'Shaheen, Uzma'
'Flörke, Ulrich'
_publ_section_title
;
 1-(2-Fluorophenyl)-3-(3,4,5-trimethoxybenzoyl)thiourea
;
_journal_coeditor_code           SI2257
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1133
_journal_paper_doi               10.1107/S160053681001408X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H17 F N2 O4 S'
_chemical_formula_moiety         'C17 H17 F N2 O4 S'
_chemical_formula_sum            'C17 H17 F N2 O4 S'
_chemical_formula_weight         364.39
_chemical_name_systematic
;
1-(2-Fluorophenyl)-3-(3,4,5-trimethoxybenzoyl)thiourea
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.092(2)
_cell_angle_beta                 90.694(2)
_cell_angle_gamma                91.712(2)
_cell_formula_units_Z            2
_cell_length_a                   4.0828(5)
_cell_length_b                   14.0420(16)
_cell_length_c                   14.2295(16)
_cell_measurement_reflns_used    2067
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.85
_cell_volume                     815.21(16)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7686
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.43
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.9567
_exptl_absorpt_correction_T_min  0.8955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.274
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0423
_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)+(0.0485P)²+0.2731P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                3128
_reflns_number_total             3868
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            si2257.cif
_cod_data_source_block           I
_cod_database_code               2225974
_cod_database_fobs_code          2225974
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
S S1 0.28840(12) 0.51052(3) 0.37700(3) 0.02191(13) Uani d . 1 . .
F F1 0.1367(3) 0.83707(8) 0.21822(8) 0.0346(3) Uani d . 1 . .
O O1 0.0156(4) 0.81511(9) 0.44315(9) 0.0287(3) Uani d . 1 . .
O O2 -0.5433(3) 0.95757(8) 0.72291(8) 0.0239(3) Uani d . 1 . .
O O3 -0.3506(3) 0.85284(8) 0.86784(8) 0.0220(3) Uani d . 1 . .
O O4 0.0054(3) 0.70067(8) 0.84415(8) 0.0228(3) Uani d . 1 . .
N N1 0.2791(4) 0.69556(10) 0.32920(10) 0.0220(3) Uani d . 1 . .
H H1A 0.2360 0.7532 0.3500 0.026 Uiso calc R 1 . .
N N2 0.0880(4) 0.65816(10) 0.47587(10) 0.0199(3) Uani d . 1 . .
H H2A 0.0559 0.6148 0.5189 0.024 Uiso calc R 1 . .
C C1 0.3979(4) 0.69150(12) 0.23660(12) 0.0199(4) Uani d . 1 . .
C C2 0.5894(5) 0.62118(13) 0.19798(13) 0.0264(4) Uani d . 1 . .
H H2B 0.6512 0.5687 0.2347 0.032 Uiso calc R 1 . .
C C3 0.6906(5) 0.62772(13) 0.10527(14) 0.0309(5) Uani d . 1 . .
H H3A 0.8210 0.5792 0.0791 0.037 Uiso calc R 1 . .
C C4 0.6043(5) 0.70389(13) 0.05025(13) 0.0279(4) Uani d . 1 . .
H H4A 0.6729 0.7071 -0.0132 0.033 Uiso calc R 1 . .
C C5 0.4183(5) 0.77486(13) 0.08855(13) 0.0271(4) Uani d . 1 . .
H H5A 0.3590 0.8279 0.0522 0.032 Uiso calc R 1 . .
C C6 0.3206(5) 0.76752(12) 0.17987(13) 0.0232(4) Uani d . 1 . .
C C7 0.2210(4) 0.62634(12) 0.39079(11) 0.0176(3) Uani d . 1 . .
C C8 0.0018(4) 0.74974(11) 0.49981(12) 0.0190(3) Uani d . 1 . .
C C9 -0.1053(4) 0.76904(11) 0.59750(11) 0.0174(3) Uani d . 1 . .
C C10 -0.2858(4) 0.85088(11) 0.61089(12) 0.0189(3) Uani d . 1 . .
H H10A -0.3518 0.8868 0.5584 0.023 Uiso calc R 1 . .
C C11 -0.3685(4) 0.87953(11) 0.70090(12) 0.0187(3) Uani d . 1 . .
C C12 -0.2668(4) 0.82639(11) 0.77787(11) 0.0182(3) Uani d . 1 . .
C C13 -0.0860(4) 0.74466(11) 0.76356(11) 0.0175(3) Uani d . 1 . .
C C14 -0.0055(4) 0.71485(11) 0.67339(12) 0.0181(3) Uani d . 1 . .
H H14A 0.1150 0.6588 0.6635 0.022 Uiso calc R 1 . .
C C15 -0.6232(5) 1.01977(12) 0.64767(13) 0.0262(4) Uani d . 1 . .
H H15A -0.7484 1.0730 0.6723 0.039 Uiso calc R 1 . .
H H15B -0.7549 0.9843 0.5999 0.039 Uiso calc R 1 . .
H H15C -0.4210 1.0444 0.6194 0.039 Uiso calc R 1 . .
C C16 -0.1525(5) 0.93050(14) 0.90583(13) 0.0296(4) Uani d . 1 . .
H H16A -0.2241 0.9460 0.9697 0.044 Uiso calc R 1 . .
H H16B -0.1753 0.9863 0.8662 0.044 Uiso calc R 1 . .
H H16C 0.0774 0.9124 0.9077 0.044 Uiso calc R 1 . .
C C17 0.1706(5) 0.61312(12) 0.83456(13) 0.0247(4) Uani d . 1 . .
H H17B 0.2231 0.5891 0.8970 0.037 Uiso calc R 1 . .
H H17C 0.3735 0.6237 0.7996 0.037 Uiso calc R 1 . .
H H17D 0.0289 0.5663 0.8004 0.037 Uiso calc R 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O2 C15 . . 117.24(13) ?
C12 O3 C16 . . 113.37(13) ?
C13 O4 C17 . . 117.45(13) ?
C7 N1 C1 . . 130.78(14) ?
C7 N1 H1A . . 114.6 ?
C1 N1 H1A . . 114.6 ?
C8 N2 C7 . . 127.44(14) ?
C8 N2 H2A . . 116.3 ?
C7 N2 H2A . . 116.3 ?
C2 C1 C6 . . 117.45(16) ?
C2 C1 N1 . . 126.57(15) ?
C6 C1 N1 . . 115.96(15) ?
C1 C2 C3 . . 119.80(17) ?
C1 C2 H2B . . 120.1 ?
C3 C2 H2B . . 120.1 ?
C4 C3 C2 . . 121.17(18) ?
C4 C3 H3A . . 119.4 ?
C2 C3 H3A . . 119.4 ?
C5 C4 C3 . . 119.40(17) ?
C5 C4 H4A . . 120.3 ?
C3 C4 H4A . . 120.3 ?
C6 C5 C4 . . 118.79(16) ?
C6 C5 H5A . . 120.6 ?
C4 C5 H5A . . 120.6 ?
F1 C6 C5 . . 119.23(15) ?
F1 C6 C1 . . 117.40(15) ?
C5 C6 C1 . . 123.38(17) ?
N1 C7 N2 . . 114.10(14) ?
N1 C7 S1 . . 127.56(13) ?
N2 C7 S1 . . 118.34(12) ?
O1 C8 N2 . . 122.03(15) ?
O1 C8 C9 . . 119.80(15) ?
N2 C8 C9 . . 118.16(14) ?
C10 C9 C14 . . 121.30(15) ?
C10 C9 C8 . . 115.80(14) ?
C14 C9 C8 . . 122.59(15) ?
C11 C10 C9 . . 119.76(15) ?
C11 C10 H10A . . 120.1 ?
C9 C10 H10A . . 120.1 ?
O2 C11 C10 . . 125.26(15) ?
O2 C11 C12 . . 115.17(14) ?
C10 C11 C12 . . 119.56(15) ?
O3 C12 C13 . . 119.38(14) ?
O3 C12 C11 . . 120.47(15) ?
C13 C12 C11 . . 120.13(15) ?
O4 C13 C14 . . 124.86(15) ?
O4 C13 C12 . . 114.50(14) ?
C14 C13 C12 . . 120.63(15) ?
C13 C14 C9 . . 118.61(15) ?
C13 C14 H14A . . 120.7 ?
C9 C14 H14A . . 120.7 ?
O2 C15 H15A . . 109.5 ?
O2 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O2 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O3 C16 H16A . . 109.5 ?
O3 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O3 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O4 C17 H17B . . 109.5 ?
O4 C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O4 C17 H17D . . 109.5 ?
H17B C17 H17D . . 109.5 ?
H17C C17 H17D . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 . 1.6659(17) ?
F1 C6 . 1.360(2) ?
O1 C8 . 1.2337(19) ?
O2 C11 . 1.359(2) ?
O2 C15 . 1.435(2) ?
O3 C12 . 1.3763(19) ?
O3 C16 . 1.432(2) ?
O4 C13 . 1.3660(19) ?
O4 C17 . 1.425(2) ?
N1 C7 . 1.339(2) ?
N1 C1 . 1.410(2) ?
N1 H1A . 0.8800 ?
N2 C8 . 1.381(2) ?
N2 C7 . 1.404(2) ?
N2 H2A . 0.8800 ?
C1 C2 . 1.387(2) ?
C1 C6 . 1.392(2) ?
C2 C3 . 1.391(3) ?
C2 H2B . 0.9500 ?
C3 C4 . 1.389(3) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.379(3) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.369(2) ?
C5 H5A . 0.9500 ?
C8 C9 . 1.485(2) ?
C9 C10 . 1.395(2) ?
C9 C14 . 1.397(2) ?
C10 C11 . 1.384(2) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.403(2) ?
C12 C13 . 1.396(2) ?
C13 C14 . 1.388(2) ?
C14 H14A . 0.9500 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C17 H17D . 0.9800 ?
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 S1 2_566 0.88 2.70 3.5219(15) 156.8
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 C2 . . . . -24.6(3) ?
C7 N1 C1 C6 . . . . 157.28(18) ?
C6 C1 C2 C3 . . . . -1.2(3) ?
N1 C1 C2 C3 . . . . -179.34(19) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . 0.8(3) ?
C3 C4 C5 C6 . . . . -0.7(3) ?
C4 C5 C6 F1 . . . . -179.93(17) ?
C4 C5 C6 C1 . . . . -0.3(3) ?
C2 C1 C6 F1 . . . . -179.10(16) ?
N1 C1 C6 F1 . . . . -0.8(3) ?
C2 C1 C6 C5 . . . . 1.3(3) ?
N1 C1 C6 C5 . . . . 179.62(18) ?
C1 N1 C7 N2 . . . . -177.33(17) ?
C1 N1 C7 S1 . . . . 2.7(3) ?
C8 N2 C7 N1 . . . . 2.9(3) ?
C8 N2 C7 S1 . . . . -177.17(14) ?
C7 N2 C8 O1 . . . . 4.8(3) ?
C7 N2 C8 C9 . . . . -174.22(16) ?
O1 C8 C9 C10 . . . . 20.7(3) ?
N2 C8 C9 C10 . . . . -160.21(16) ?
O1 C8 C9 C14 . . . . -152.96(18) ?
N2 C8 C9 C14 . . . . 26.1(3) ?
C14 C9 C10 C11 . . . . 0.0(3) ?
C8 C9 C10 C11 . . . . -173.74(15) ?
C15 O2 C11 C10 . . . . -5.8(3) ?
C15 O2 C11 C12 . . . . 173.60(15) ?
C9 C10 C11 O2 . . . . -179.91(16) ?
C9 C10 C11 C12 . . . . 0.7(3) ?
C16 O3 C12 C13 . . . . 102.98(18) ?
C16 O3 C12 C11 . . . . -78.6(2) ?
O2 C11 C12 O3 . . . . 1.5(2) ?
C10 C11 C12 O3 . . . . -179.01(15) ?
O2 C11 C12 C13 . . . . 179.89(15) ?
C10 C11 C12 C13 . . . . -0.6(3) ?
C17 O4 C13 C14 . . . . -5.9(2) ?
C17 O4 C13 C12 . . . . 175.70(15) ?
O3 C12 C13 O4 . . . . -3.2(2) ?
C11 C12 C13 O4 . . . . 178.39(15) ?
O3 C12 C13 C14 . . . . 178.27(15) ?
C11 C12 C13 C14 . . . . -0.1(3) ?
O4 C13 C14 C9 . . . . -177.53(16) ?
C12 C13 C14 C9 . . . . 0.8(3) ?
C10 C9 C14 C13 . . . . -0.8(3) ?
C8 C9 C14 C13 . . . . 172.57(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 968363
