#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/02/2210231.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_2210231
loop_
_publ_author_name
'Yesilkaynak, Tuncay'
'Flörke, Ulrich'
'Külcü, Nevzat'
'Arslan, Hakan'
_publ_section_title
;
 1-Benzoyl-3-(4-methylpyridin-2-yl)thiourea
;
_journal_coeditor_code           GA2001
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3934
_journal_page_last               o3935
_journal_paper_doi               10.1107/S1600536806032302
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H13 N3 O S'
_chemical_formula_moiety         'C14 H13 N3 O S'
_chemical_formula_sum            'C14 H13 N3 O S'
_chemical_formula_weight         271.33
_chemical_name_systematic
;
1-Benzoyl-3-(4-methylpyridin-2-yl)thiourea
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.962(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9247(15)
_cell_length_b                   5.1952(7)
_cell_length_c                   21.615(3)
_cell_measurement_reflns_used    1567
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.40
_cell_volume                     1329.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2002)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_sigmaI/netI    0.0925
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11451
_diffrn_reflns_theta_full        28.20
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  430
_diffrn_standards_number         1560
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.9708
_exptl_absorpt_correction_T_min  0.9119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0499
_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)+(0.044P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                2026
_reflns_number_total             3254
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ga2001.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210231
_cod_database_fobs_code          2210231
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
S S1 0.02463(4) 0.69073(13) 0.08562(2) 0.03769(19) Uani d . 1
O O1 0.37889(11) 0.4364(3) 0.05884(7) 0.0405(4) Uani d . 1
N N1 0.36791(13) 0.9156(3) 0.19281(8) 0.0344(4) Uani d . 1
N N2 0.24871(13) 0.7134(3) 0.12008(7) 0.0291(4) Uani d . 1
H H2B 0.3135 0.6469 0.1125 0.035 Uiso calc R 1
N N3 0.18649(12) 0.4287(3) 0.04268(7) 0.0278(4) Uani d . 1
H H3A 0.1288 0.3511 0.0212 0.033 Uiso calc R 1
C C1 0.39131(18) 1.0899(5) 0.23789(10) 0.0404(6) Uani d . 1
H H1A 0.4670 1.1023 0.2573 0.048 Uiso calc R 1
C C2 0.31223(18) 1.2523(4) 0.25788(10) 0.0394(6) Uani d . 1
H H2A 0.3336 1.3736 0.2900 0.047 Uiso calc R 1
C C3 0.20114(17) 1.2376(4) 0.23071(9) 0.0321(5) Uani d . 1
C C4 0.17485(16) 1.0588(4) 0.18362(9) 0.0292(5) Uani d . 1
H H4A 0.1000 1.0442 0.1632 0.035 Uiso calc R 1
C C5 0.26024(16) 0.9021(4) 0.16702(8) 0.0278(5) Uani d . 1
C C6 0.11200(18) 1.4089(5) 0.25197(10) 0.0411(6) Uani d . 1
H H6A 0.0897 1.3430 0.2912 0.062 Uiso calc R 1
H H6B 0.0460 1.4120 0.2202 0.062 Uiso calc R 1
H H6C 0.1420 1.5837 0.2584 0.062 Uiso calc R 1
C C7 0.15969(15) 0.6142(4) 0.08464(8) 0.0276(5) Uani d . 1
C C8 0.29257(16) 0.3499(4) 0.03026(9) 0.0290(5) Uani d . 1
C C9 0.29646(15) 0.1549(4) -0.01933(8) 0.0272(5) Uani d . 1
C C10 0.20970(17) -0.0189(4) -0.03680(9) 0.0313(5) Uani d . 1
H H10A 0.1419 -0.0111 -0.0179 0.038 Uiso calc R 1
C C11 0.22211(19) -0.2024(4) -0.08146(10) 0.0382(5) Uani d . 1
H H11A 0.1624 -0.3197 -0.0937 0.046 Uiso calc R 1
C C12 0.3210(2) -0.2163(4) -0.10846(10) 0.0400(6) Uani d . 1
H H12A 0.3296 -0.3451 -0.1387 0.048 Uiso calc R 1
C C13 0.40745(18) -0.0440(4) -0.09172(9) 0.0370(5) Uani d . 1
H H13A 0.4750 -0.0531 -0.1108 0.044 Uiso calc R 1
C C14 0.39563(16) 0.1413(4) -0.04727(9) 0.0320(5) Uani d . 1
H H14A 0.4552 0.2598 -0.0357 0.038 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C5 116.43(18) ?
C7 N2 C5 133.23(17) y
C7 N2 H2B 113.4 ?
C5 N2 H2B 113.4 ?
C8 N3 C7 128.30(16) y
C8 N3 H3A 115.9 ?
C7 N3 H3A 115.9 ?
N1 C1 C2 123.76(19) ?
N1 C1 H1A 118.1 ?
C2 C1 H1A 118.1 ?
C1 C2 C3 119.4(2) ?
C1 C2 H2A 120.3 ?
C3 C2 H2A 120.3 ?
C2 C3 C4 117.93(19) ?
C2 C3 C6 120.94(19) ?
C4 C3 C6 121.13(18) ?
C5 C4 C3 118.47(18) ?
C5 C4 H4A 120.8 ?
C3 C4 H4A 120.8 ?
N1 C5 C4 124.02(18) ?
N1 C5 N2 110.03(17) ?
C4 C5 N2 125.92(17) ?
C3 C6 H6A 109.5 ?
C3 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C3 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
N2 C7 N3 114.41(16) y
N2 C7 S1 127.22(16) ?
N3 C7 S1 118.37(13) ?
O1 C8 N3 121.78(19) ?
O1 C8 C9 121.35(17) ?
N3 C8 C9 116.87(16) y
C10 C9 C14 119.47(19) ?
C10 C9 C8 123.63(18) ?
C14 C9 C8 116.84(18) ?
C11 C10 C9 120.0(2) ?
C11 C10 H10A 120.0 ?
C9 C10 H10A 120.0 ?
C10 C11 C12 120.2(2) ?
C10 C11 H11A 119.9 ?
C12 C11 H11A 119.9 ?
C11 C12 C13 120.3(2) ?
C11 C12 H12A 119.8 ?
C13 C12 H12A 119.8 ?
C14 C13 C12 119.9(2) ?
C14 C13 H13A 120.0 ?
C12 C13 H13A 120.0 ?
C13 C14 C9 120.1(2) ?
C13 C14 H14A 120.0 ?
C9 C14 H14A 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 1.6616(19) y
O1 C8 1.220(2) n
N1 C1 1.334(3) ?
N1 C5 1.338(2) ?
N2 C7 1.335(2) y
N2 C5 1.406(2) y
N2 H2B 0.8800 ?
N3 C8 1.386(2) y
N3 C7 1.387(2) y
N3 H3A 0.8800 ?
C1 C2 1.374(3) ?
C1 H1A 0.9500 ?
C2 C3 1.385(3) ?
C2 H2A 0.9500 ?
C3 C4 1.385(3) ?
C3 C6 1.501(3) ?
C4 C5 1.385(3) ?
C4 H4A 0.9500 ?
C6 H6A 0.9800 ?
C6 H6B 0.9800 ?
C6 H6C 0.9800 ?
C8 C9 1.480(3) y
C9 C10 1.391(3) ?
C9 C14 1.393(3) ?
C10 C11 1.377(3) ?
C10 H10A 0.9500 ?
C11 C12 1.380(3) ?
C11 H11A 0.9500 ?
C12 C13 1.380(3) ?
C12 H12A 0.9500 ?
C13 C14 1.379(3) ?
C13 H13A 0.9500 ?
C14 H14A 0.9500 ?
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 H2B O1 . 0.88 1.83 2.594(2) 143
N3 H3A S1 3_565 0.88 2.77 3.567(2) 150
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
C5 N1 C1 C2 -0.6(3)
N1 C1 C2 C3 0.3(3)
C1 C2 C3 C4 -0.6(3)
C1 C2 C3 C6 179.0(2)
C2 C3 C4 C5 1.1(3)
C6 C3 C4 C5 -178.53(19)
C1 N1 C5 C4 1.2(3)
C1 N1 C5 N2 179.31(18)
C3 C4 C5 N1 -1.5(3)
C3 C4 C5 N2 -179.29(18)
C7 N2 C5 N1 174.1(2)
C7 N2 C5 C4 -7.9(3)
C5 N2 C7 N3 179.47(18)
C5 N2 C7 S1 0.0(3)
C8 N3 C7 N2 -5.2(3)
C8 N3 C7 S1 174.38(16)
C7 N3 C8 O1 2.9(3)
C7 N3 C8 C9 -177.27(17)
O1 C8 C9 C10 154.7(2)
N3 C8 C9 C10 -25.2(3)
O1 C8 C9 C14 -22.3(3)
N3 C8 C9 C14 157.83(17)
C14 C9 C10 C11 -0.1(3)
C8 C9 C10 C11 -176.99(18)
C9 C10 C11 C12 0.7(3)
C10 C11 C12 C13 -1.1(3)
C11 C12 C13 C14 0.7(3)
C12 C13 C14 C9 -0.1(3)
C10 C9 C14 C13 -0.2(3)
C8 C9 C14 C13 176.87(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 769860
