#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/93/2239363.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_2239363
loop_
_publ_author_name
'Awang, Nor Wahida.'
'Hasbullah, Siti Aishah'
'Yusoff, Siti Fairus M.'
'Yamin, Bohari M.'
_publ_section_title
;
 N-[Ethyl(2-hydroxyethyl)carbamothioyl]-3-fluorobenzamide
;
_journal_coeditor_code           BQ2395
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o570
_journal_paper_doi               10.1107/S1600536814008174
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C12 H15 F N2 O2 S'
_chemical_formula_moiety         'C12 H15 F N2 O2 S'
_chemical_formula_sum            'C12 H15 F N2 O2 S'
_chemical_formula_weight         270.32
_chemical_name_systematic
;
N-[Ethyl(2-hydroxyethyl)carbamothioyl]-3-fluorobenzamide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0205(3)
_cell_length_b                   12.9441(6)
_cell_length_c                   17.1071(9)
_cell_measurement_reflns_used    11689
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      3.1
_cell_volume                     1333.16(11)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL2013 (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       'ω 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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21708
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.2
_diffrn_reflns_theta_min         3.1
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.9309
_exptl_absorpt_correction_T_min  0.8850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.175
_refine_ls_abs_structure_details 'Flack (1983), 1378 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0367P)²+0.3143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                2864
_reflns_number_total             3290
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2395sup1.cif
_cod_data_source_block           I
_cod_database_code               2239363
_cod_database_fobs_code          2239363
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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_symmetry_multiplicity
F F1 -0.5492(2) 0.22048(12) 0.06124(8) 0.0690(4) Uani d . 1 1
S S1 0.25957(10) 0.08756(4) 0.35274(3) 0.05288(15) Uani d . 1 1
O O1 0.2778(3) 0.02641(9) 0.17285(8) 0.0537(4) Uani d . 1 1
O O2 0.0320(2) 0.39036(10) 0.21034(9) 0.0501(3) Uani d D 1 1
H H2A -0.053(3) 0.4382(14) 0.2024(14) 0.067(7) Uiso d D 1 1
N N1 0.1564(2) 0.18174(10) 0.21762(8) 0.0369(3) Uani d . 1 1
H H1A 0.0836 0.2359 0.2039 0.044 Uiso calc R 1 1
N N2 0.3727(2) 0.27479(10) 0.30261(8) 0.0360(3) Uani d . 1 1
C C1 -0.2089(3) 0.16654(13) 0.11163(9) 0.0382(4) Uani d . 1 1
H H1 -0.2228 0.2134 0.1526 0.046 Uiso calc R 1 1
C C2 -0.3693(3) 0.15905(16) 0.05543(10) 0.0438(4) Uani d . 1 1
C C3 -0.3574(4) 0.09202(19) -0.00610(11) 0.0556(5) Uani d . 1 1
H H3 -0.4698 0.0890 -0.0433 0.067 Uiso calc R 1 1
C C4 -0.1751(4) 0.02952(18) -0.01123(13) 0.0625(6) Uani d . 1 1
H H4 -0.1633 -0.0167 -0.0526 0.075 Uiso calc R 1 1
C C5 -0.0084(4) 0.03385(15) 0.04385(11) 0.0497(5) Uani d . 1 1
H H5 0.1148 -0.0091 0.0394 0.060 Uiso calc R 1 1
C C6 -0.0245(3) 0.10242(12) 0.10612(10) 0.0341(3) Uani d . 1 1
C C7 0.1516(3) 0.09866(12) 0.16784(10) 0.0349(3) Uani d . 1 1
C C8 0.2701(3) 0.18551(11) 0.28899(10) 0.0348(3) Uani d . 1 1
C C9 0.4712(4) 0.29815(16) 0.37932(11) 0.0546(5) Uani d . 1 1
H H9A 0.3884 0.2621 0.4196 0.066 Uiso calc R 1 1
H H9B 0.4587 0.3717 0.3893 0.066 Uiso calc R 1 1
C C10 0.7126(4) 0.26688(19) 0.38404(16) 0.0765(8) Uani d . 1 1
H H10A 0.7259 0.1941 0.3743 0.115 Uiso calc R 1 1
H H10B 0.7690 0.2823 0.4352 0.115 Uiso calc R 1 1
H H10C 0.7964 0.3044 0.3456 0.115 Uiso calc R 1 1
C C11 0.4091(3) 0.35433(13) 0.24232(10) 0.0366(4) Uani d . 1 1
H H11A 0.4176 0.3211 0.1916 0.044 Uiso calc R 1 1
H H11B 0.5505 0.3879 0.2520 0.044 Uiso calc R 1 1
C C12 0.2301(4) 0.43491(12) 0.24008(11) 0.0447(4) Uani d . 1 1
H H12A 0.2041 0.4615 0.2923 0.054 Uiso calc R 1 1
H H12B 0.2760 0.4919 0.2070 0.054 Uiso calc R 1 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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C12 O2 H2A 106.3(18)
C7 N1 C8 125.36(13)
C7 N1 H1A 117.3
C8 N1 H1A 117.3
C8 N2 C9 121.44(15)
C8 N2 C11 123.58(14)
C9 N2 C11 114.88(14)
C2 C1 C6 118.34(16)
C2 C1 H1 120.8
C6 C1 H1 120.8
F1 C2 C3 118.29(17)
F1 C2 C1 118.32(16)
C3 C2 C1 123.38(18)
C2 C3 C4 117.89(18)
C2 C3 H3 121.1
C4 C3 H3 121.1
C3 C4 C5 121.14(19)
C3 C4 H4 119.4
C5 C4 H4 119.4
C4 C5 C6 120.0(2)
C4 C5 H5 120.0
C6 C5 H5 120.0
C1 C6 C5 119.29(16)
C1 C6 C7 122.51(15)
C5 C6 C7 118.06(16)
O1 C7 N1 123.33(15)
O1 C7 C6 121.38(15)
N1 C7 C6 115.29(14)
N2 C8 N1 114.19(13)
N2 C8 S1 124.15(13)
N1 C8 S1 121.54(12)
N2 C9 C10 112.35(19)
N2 C9 H9A 109.1
C10 C9 H9A 109.1
N2 C9 H9B 109.1
C10 C9 H9B 109.1
H9A C9 H9B 107.9
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N2 C11 C12 113.38(15)
N2 C11 H11A 108.9
C12 C11 H11A 108.9
N2 C11 H11B 108.9
C12 C11 H11B 108.9
H11A C11 H11B 107.7
O2 C12 C11 109.28(13)
O2 C12 H12A 109.8
C11 C12 H12A 109.8
O2 C12 H12B 109.8
C11 C12 H12B 109.8
H12A C12 H12B 108.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.347(2)
S1 C8 1.6736(16)
O1 C7 1.208(2)
O2 C12 1.419(2)
O2 H2A 0.816(10)
N1 C7 1.372(2)
N1 C8 1.401(2)
N1 H1A 0.8600
N2 C8 1.331(2)
N2 C9 1.471(2)
N2 C11 1.474(2)
C1 C2 1.366(2)
C1 C6 1.389(2)
C1 H1 0.9300
C2 C3 1.366(3)
C3 C4 1.366(3)
C3 H3 0.9300
C4 C5 1.377(3)
C4 H4 0.9300
C5 C6 1.390(2)
C5 H5 0.9300
C6 C7 1.497(2)
C9 C10 1.511(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 C12 1.500(3)
C11 H11A 0.9700
C11 H11B 0.9700
C12 H12A 0.9700
C12 H12B 0.9700
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
_geom_hbond_publ_flag
N1 H1A O2 1_555 0.86 2.03 2.805(2) 150 yes
C9 H9A S1 1_555 0.97 2.65 3.043(3) 105 no
O2 H2A S1 3_555 0.82(3) 2.49(3) 3.2805(19) 166(3) yes
C11 H11B O1 3_655 0.97 2.44 3.259(3) 142 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
C6 C1 C2 F1 179.31(16)
C6 C1 C2 C3 -0.2(3)
F1 C2 C3 C4 -179.56(19)
C1 C2 C3 C4 0.0(3)
C2 C3 C4 C5 0.0(3)
C3 C4 C5 C6 0.2(3)
C2 C1 C6 C5 0.5(2)
C2 C1 C6 C7 -175.11(16)
C4 C5 C6 C1 -0.5(3)
C4 C5 C6 C7 175.31(19)
C8 N1 C7 O1 -14.3(3)
C8 N1 C7 C6 165.10(16)
C1 C6 C7 O1 160.93(17)
C5 C6 C7 O1 -14.7(2)
C1 C6 C7 N1 -18.5(2)
C5 C6 C7 N1 165.87(16)
C9 N2 C8 N1 170.60(17)
C11 N2 C8 N1 -13.3(2)
C9 N2 C8 S1 -5.4(3)
C11 N2 C8 S1 170.74(13)
C7 N1 C8 N2 139.06(17)
C7 N1 C8 S1 -44.8(2)
C8 N2 C9 C10 91.8(2)
C11 N2 C9 C10 -84.6(2)
C8 N2 C11 C12 93.48(19)
C9 N2 C11 C12 -90.17(19)
N2 C11 C12 O2 -70.51(19)
