#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/69/2216985.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_2216985
loop_
_publ_author_name
'Dong Liang'
'Li-Xing Gao'
'Yan Gao'
'Jing Xu'
'Wei Wang'
_publ_section_title
2-(4,6-Dimethylpyrimidin-2-ylsulfanyl)-N-(4-methylpyridin-2-yl)acetamide
_journal_coeditor_code           CI2528
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o201
_journal_page_last               o201
_journal_paper_doi               10.1107/S1600536807064082
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H16 N4 O S'
_chemical_formula_moiety         'C14 H16 N4 O S'
_chemical_formula_sum            'C14 H16 N4 O S'
_chemical_formula_weight         288.37
_chemical_melting_point          418
_chemical_name_systematic
2-(4,6-Dimethylpyrimidin-2-ylsulfanyl)-N-(4-methylpyridin-2-yl)acetamide
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 91.678(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1924(19)
_cell_length_b                   15.423(5)
_cell_length_c                   18.121(6)
_cell_measurement_reflns_used    1663
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.24
_cell_measurement_theta_min      2.61
_cell_volume                     1450.6(9)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_sigmaI/netI    0.0706
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8084
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.73
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.9565
_exptl_absorpt_correction_T_min  0.9156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.226
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2970
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0718P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                1582
_reflns_number_total             2970
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2528.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1450.5(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2216985
_cod_database_fobs_code          2216985
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 0.19772(16) 0.06150(5) 0.30190(4) 0.0565(3) Uani d . 1
O O1 0.4584(4) 0.17627(12) 0.39721(11) 0.0629(6) Uani d . 1
C C8 0.5502(6) 0.10500(16) 0.40685(14) 0.0424(7) Uani d . 1
N N3 0.7497(4) 0.08705(13) 0.45581(11) 0.0437(6) Uani d . 1
H H3A 0.7929 0.0334 0.4603 0.052 Uiso calc R 1
N N1 -0.0905(5) -0.02849(15) 0.21206(12) 0.0526(6) Uani d . 1
N N2 0.2279(4) -0.11038(14) 0.28121(12) 0.0487(6) Uani d . 1
N N4 1.0824(5) 0.11059(13) 0.54011(12) 0.0471(6) Uani d . 1
C C7 0.4517(5) 0.02656(16) 0.36422(15) 0.0466(7) Uani d . 1
H H7A 0.3873 -0.0166 0.3980 0.056 Uiso calc R 1
H H7B 0.5901 0.0008 0.3369 0.056 Uiso calc R 1
C C1 0.1057(6) -0.03772(17) 0.26160(15) 0.0464(7) Uani d . 1
C C9 0.8914(5) 0.14679(15) 0.49939(13) 0.0390(7) Uani d . 1
C C10 0.8368(6) 0.23511(16) 0.50028(15) 0.0493(7) Uani d . 1
H H10 0.7006 0.2572 0.4716 0.059 Uiso calc R 1
C C3 -0.0551(6) -0.18068(19) 0.19480(16) 0.0566(8) Uani d . 1
H H3 -0.1119 -0.2310 0.1712 0.068 Uiso calc R 1
C C12 1.1828(6) 0.25295(18) 0.58610(17) 0.0580(8) Uani d . 1
H H12 1.2871 0.2874 0.6167 0.070 Uiso calc R 1
C C4 0.1449(6) -0.18362(18) 0.24637(16) 0.0502(7) Uani d . 1
C C2 -0.1703(6) -0.1016(2) 0.17864(15) 0.0535(8) Uani d . 1
C C5 0.2828(6) -0.26511(18) 0.26755(19) 0.0677(9) Uani d . 1
H H5A 0.4476 -0.2663 0.2449 0.102 Uiso calc R 1
H H5B 0.1828 -0.3142 0.2511 0.102 Uiso calc R 1
H H5C 0.3067 -0.2673 0.3202 0.102 Uiso calc R 1
C C13 1.2229(6) 0.16531(18) 0.58239(17) 0.0611(9) Uani d . 1
H H13 1.3570 0.1421 0.6112 0.073 Uiso calc R 1
C C6 -0.3885(7) -0.0931(2) 0.12243(18) 0.0747(10) Uani d . 1
H H6A -0.5028 -0.0478 0.1372 0.112 Uiso calc R 1
H H6B -0.4812 -0.1469 0.1191 0.112 Uiso calc R 1
H H6C -0.3205 -0.0792 0.0752 0.112 Uiso calc R 1
C C11 0.9856(6) 0.28937(17) 0.54384(15) 0.0507(8) Uani d . 1
C C14 0.9279(7) 0.38546(17) 0.54669(19) 0.0782(11) Uani d . 1
H H14A 0.8268 0.3977 0.5890 0.117 Uiso calc R 1
H H14B 0.8337 0.4023 0.5026 0.117 Uiso calc R 1
H H14C 1.0866 0.4173 0.5503 0.117 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
C1 S1 C7 100.72(13)
O1 C8 N3 124.3(2)
O1 C8 C7 121.8(3)
N3 C8 C7 113.9(2)
C8 N3 C9 127.1(2)
C8 N3 H3A 116.5
C9 N3 H3A 116.5
C2 N1 C1 115.5(2)
C1 N2 C4 115.7(2)
C9 N4 C13 115.7(2)
C8 C7 S1 108.17(18)
C8 C7 H7A 110.1
S1 C7 H7A 110.1
C8 C7 H7B 110.1
S1 C7 H7B 110.1
H7A C7 H7B 108.4
N2 C1 N1 127.8(2)
N2 C1 S1 120.1(2)
N1 C1 S1 112.1(2)
N4 C9 C10 123.3(2)
N4 C9 N3 113.7(2)
C10 C9 N3 123.0(2)
C11 C10 C9 119.5(2)
C11 C10 H10 120.3
C9 C10 H10 120.3
C4 C3 C2 119.0(3)
C4 C3 H3 120.5
C2 C3 H3 120.5
C13 C12 C11 119.1(3)
C13 C12 H12 120.5
C11 C12 H12 120.5
N2 C4 C3 120.7(3)
N2 C4 C5 116.0(3)
C3 C4 C5 123.3(3)
N1 C2 C3 121.3(3)
N1 C2 C6 116.6(3)
C3 C2 C6 122.1(3)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N4 C13 C12 124.6(3)
N4 C13 H13 117.7
C12 C13 H13 117.7
C2 C6 H6A 109.5
C2 C6 H6B 109.5
H6A C6 H6B 109.5
C2 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C10 C11 C12 117.8(2)
C10 C11 C14 120.5(3)
C12 C11 C14 121.6(3)
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.756(3)
S1 C7 1.794(3)
O1 C8 1.209(3)
C8 N3 1.372(3)
C8 C7 1.516(3)
N3 C9 1.407(3)
N3 H3A 0.86
N1 C2 1.340(3)
N1 C1 1.346(3)
N2 C1 1.331(3)
N2 C4 1.358(3)
N4 C9 1.341(3)
N4 C13 1.341(3)
C7 H7A 0.97
C7 H7B 0.97
C9 C10 1.391(3)
C10 C11 1.373(4)
C10 H10 0.93
C3 C4 1.377(4)
C3 C2 1.386(4)
C3 H3 0.93
C12 C13 1.369(4)
C12 C11 1.380(4)
C12 H12 0.93
C4 C5 1.491(4)
C2 C6 1.507(4)
C5 H5A 0.96
C5 H5B 0.96
C5 H5C 0.96
C13 H13 0.93
C6 H6A 0.96
C6 H6B 0.96
C6 H6C 0.96
C11 C14 1.513(4)
C14 H14A 0.96
C14 H14B 0.96
C14 H14C 0.96
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
N3 H3A N4 3_756 0.86 2.31 3.171(3) 174
C10 H10 O1 . 0.93 2.20 2.821(4) 123
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
O1 C8 N3 C9 -4.1(5)
C7 C8 N3 C9 175.6(2)
O1 C8 C7 S1 0.8(4)
N3 C8 C7 S1 -178.85(19)
C1 S1 C7 C8 -177.95(19)
C4 N2 C1 N1 0.6(4)
C4 N2 C1 S1 -179.3(2)
C2 N1 C1 N2 -0.2(4)
C2 N1 C1 S1 179.6(2)
C7 S1 C1 N2 -1.0(3)
C7 S1 C1 N1 179.1(2)
C13 N4 C9 C10 -0.5(4)
C13 N4 C9 N3 179.8(2)
C8 N3 C9 N4 -177.6(2)
C8 N3 C9 C10 2.8(4)
N4 C9 C10 C11 0.9(4)
N3 C9 C10 C11 -179.4(2)
C1 N2 C4 C3 -0.5(4)
C1 N2 C4 C5 179.4(3)
C2 C3 C4 N2 0.2(4)
C2 C3 C4 C5 -179.7(3)
C1 N1 C2 C3 -0.1(4)
C1 N1 C2 C6 -179.5(3)
C4 C3 C2 N1 0.1(5)
C4 C3 C2 C6 179.5(3)
C9 N4 C13 C12 0.1(4)
C11 C12 C13 N4 -0.1(5)
C9 C10 C11 C12 -0.9(4)
C9 C10 C11 C14 -179.1(3)
C13 C12 C11 C10 0.5(5)
C13 C12 C11 C14 178.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 357043
