#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/93/2229348.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_2229348
loop_
_publ_author_name
'Wang, Chuan-Hu'
_publ_section_title
;
 Ethyl 2-{[4-(pyridin-4-yl)pyrimidin-2-yl]sulfanyl}acetate
;
_journal_coeditor_code           CV5047
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o690
_journal_paper_doi               10.1107/S1600536811004272
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H13 N3 O2 S'
_chemical_formula_moiety         'C13 H13 N3 O2 S'
_chemical_formula_sum            'C13 H13 N3 O2 S'
_chemical_formula_weight         275.33
_chemical_name_systematic
;
Ethyl 2-{[4-(pyridin-4-yl)pyrimidin-2-yl]sulfanyl}acetate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                62.661(6)
_cell_angle_beta                 71.416(5)
_cell_angle_gamma                65.024(6)
_cell_formula_units_Z            2
_cell_length_a                   8.6579(8)
_cell_length_b                   9.7394(9)
_cell_length_c                   9.9188(8)
_cell_measurement_reflns_used    3021
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.3
_cell_volume                     665.35(11)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11760
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288.0
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.199
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0379
_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)+(0.0658P)²+0.0670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                2387
_reflns_number_total             3021
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5047.cif
_cod_data_source_block           I
_cod_original_cell_volume        665.35(10)
_cod_database_code               2229348
_cod_database_fobs_code          2229348
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
C C1 0.21141(18) 0.00339(18) 0.89933(17) 0.0411(3) Uani d . 1 . .
C C2 0.3174(2) -0.21822(19) 1.10105(19) 0.0496(4) Uani d . 1 . .
H H2 0.3517 -0.3308 1.1555 0.060 Uiso calc R 1 . .
C C3 0.3336(2) -0.12042(18) 1.15846(18) 0.0459(4) Uani d . 1 . .
H H3 0.3793 -0.1652 1.2484 0.055 Uiso calc R 1 . .
C C4 0.27871(17) 0.04721(17) 1.07653(16) 0.0376(3) Uani d . 1 . .
C C5 0.28647(18) 0.16653(17) 1.12645(16) 0.0388(3) Uani d . 1 . .
C C6 0.3582(2) 0.1176(2) 1.25464(18) 0.0478(4) Uani d . 1 . .
H H6 0.4018 0.0070 1.3141 0.057 Uiso calc R 1 . .
C C7 0.3641(2) 0.2347(2) 1.2930(2) 0.0568(4) Uani d . 1 . .
H H7 0.4126 0.1991 1.3794 0.068 Uiso calc R 1 . .
C C8 0.2241(2) 0.3332(2) 1.04370(19) 0.0525(4) Uani d . 1 . .
H H8 0.1740 0.3725 0.9573 0.063 Uiso calc R 1 . .
C C9 0.2372(3) 0.4407(2) 1.0913(2) 0.0660(5) Uani d . 1 . .
H H9 0.1960 0.5521 1.0335 0.079 Uiso calc R 1 . .
C C10 0.0836(2) 0.2913(2) 0.6641(2) 0.0515(4) Uani d . 1 . .
H H10A 0.0315 0.3439 0.5718 0.062 Uiso calc R 1 . .
H H10B -0.0042 0.3227 0.7439 0.062 Uiso calc R 1 . .
C C11 0.2273(2) 0.35667(18) 0.63290(16) 0.0422(3) Uani d . 1 . .
C C12 0.2788(2) 0.5879(2) 0.6083(2) 0.0620(5) Uani d . 1 . .
H H12A 0.3426 0.6012 0.5056 0.074 Uiso calc R 1 . .
H H12B 0.3603 0.5258 0.6805 0.074 Uiso calc R 1 . .
C C13 0.1774(3) 0.7498(3) 0.6187(3) 0.0927(8) Uani d . 1 . .
H H13A 0.1014 0.8124 0.5432 0.139 Uiso calc R 1 . .
H H13B 0.2542 0.8066 0.6002 0.139 Uiso calc R 1 . .
H H13C 0.1108 0.7354 0.7193 0.139 Uiso calc R 1 . .
N N1 0.3051(2) 0.39441(19) 1.21466(18) 0.0644(4) Uani d . 1 . .
N N2 0.21695(15) 0.11055(14) 0.94434(14) 0.0392(3) Uani d . 1 . .
N N3 0.25523(17) -0.15909(16) 0.97173(16) 0.0482(3) Uani d . 1 . .
O O1 0.37818(15) 0.29263(14) 0.59842(13) 0.0516(3) Uani d . 1 . .
O O2 0.15904(14) 0.50272(13) 0.64426(13) 0.0512(3) Uani d . 1 . .
S S1 0.14603(6) 0.07492(5) 0.72151(5) 0.05259(16) Uani d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N3 . . 127.86(14) ?
N2 C1 S1 . . 118.93(11) ?
N3 C1 S1 . . 113.18(10) ?
N3 C2 C3 . . 123.15(14) ?
N3 C2 H2 . . 118.4 ?
C3 C2 H2 . . 118.4 ?
C2 C3 C4 . . 117.32(15) ?
C2 C3 H3 . . 121.3 ?
C4 C3 H3 . . 121.3 ?
N2 C4 C3 . . 120.88(13) ?
N2 C4 C5 . . 116.22(12) ?
C3 C4 C5 . . 122.90(13) ?
C8 C5 C6 . . 116.98(13) ?
C8 C5 C4 . . 120.72(13) ?
C6 C5 C4 . . 122.29(13) ?
C7 C6 C5 . . 119.32(15) ?
C7 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
N1 C7 C6 . . 124.28(16) ?
N1 C7 H7 . . 117.9 ?
C6 C7 H7 . . 117.9 ?
C9 C8 C5 . . 119.20(15) ?
C9 C8 H8 . . 120.4 ?
C5 C8 H8 . . 120.4 ?
N1 C9 C8 . . 124.07(17) ?
N1 C9 H9 . . 118.0 ?
C8 C9 H9 . . 118.0 ?
C11 C10 S1 . . 115.61(11) ?
C11 C10 H10A . . 108.4 ?
S1 C10 H10A . . 108.4 ?
C11 C10 H10B . . 108.4 ?
S1 C10 H10B . . 108.4 ?
H10A C10 H10B . . 107.4 ?
O1 C11 O2 . . 124.33(14) ?
O1 C11 C10 . . 126.61(14) ?
O2 C11 C10 . . 109.02(13) ?
O2 C12 C13 . . 107.85(15) ?
O2 C12 H12A . . 110.1 ?
C13 C12 H12A . . 110.1 ?
O2 C12 H12B . . 110.1 ?
C13 C12 H12B . . 110.1 ?
H12A C12 H12B . . 108.5 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C7 N1 C9 . . 116.14(14) ?
C1 N2 C4 . . 116.09(12) ?
C2 N3 C1 . . 114.65(12) ?
C11 O2 C12 . . 116.28(12) ?
C1 S1 C10 . . 101.64(7) ?
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
C1 N2 . 1.3323(17) ?
C1 N3 . 1.3367(19) ?
C1 S1 . 1.7582(16) ?
C2 N3 . 1.329(2) ?
C2 C3 . 1.383(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.387(2) ?
C3 H3 . 0.9300 ?
C4 N2 . 1.3456(18) ?
C4 C5 . 1.4886(19) ?
C5 C8 . 1.385(2) ?
C5 C6 . 1.388(2) ?
C6 C7 . 1.381(2) ?
C6 H6 . 0.9300 ?
C7 N1 . 1.325(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.385(2) ?
C8 H8 . 0.9300 ?
C9 N1 . 1.332(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.514(2) ?
C10 S1 . 1.7858(16) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 O1 . 1.1984(18) ?
C11 O2 . 1.3342(17) ?
C12 O2 . 1.4529(19) ?
C12 C13 . 1.479(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
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
C3 H3 O1 2_657 0.93 2.52 3.383(2) 154
C7 H7 O1 1_556 0.93 2.61 3.373(2) 140
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656516
