#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/42/2224287.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_2224287
loop_
_publ_author_name
'Neuenfeldt, Patrícia D.'
'Drawanz, Bruna B.'
'Cunico, Wilson'
'Tiekink, Edward R. T.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
_publ_section_title
;
 4-(Pyrimidin-2-yl)-1-thia-4-azaspiro[4.5]decan-3-one
;
_journal_coeditor_code           HG2601
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3190
_journal_page_last               o3191
_journal_paper_doi               10.1107/S1600536809049460
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H15 N3 O S'
_chemical_formula_moiety         'C12 H15 N3 O S'
_chemical_formula_sum            'C12 H15 N3 O S'
_chemical_formula_weight         249.33
_chemical_name_systematic
;
4-(Pyrimidin-2-yl)-1-thia-4-azaspiro[4.5]decan-3-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 95.6980(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2466(2)
_cell_length_b                   8.6748(2)
_cell_length_c                   22.0439(6)
_cell_measurement_reflns_used    7514
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1188.61(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_av_sigmaI/netI    0.039
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14004
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.0
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.40
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.14
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.14
_refine_ls_R_factor_all          0.050
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0508P)²+0.5459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.100
_refine_ls_wR_factor_ref         0.113
_reflns_number_gt                2227
_reflns_number_total             2661
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2601.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224287
_cod_database_fobs_code          2224287
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.30913(6) 0.59301(5) 0.14394(2) 0.02184(17) Uani d . 1 . .
O O1 0.19102(19) 0.33684(15) 0.00174(6) 0.0215(3) Uani d . 1 . .
N N1 -0.2660(2) 0.24603(17) 0.08348(7) 0.0189(3) Uani d . 1 . .
N N2 0.0587(2) 0.09881(17) 0.08941(8) 0.0206(3) Uani d . 1 . .
N N3 0.0732(2) 0.36704(16) 0.09593(6) 0.0147(3) Uani d . 1 . .
C C2 0.0699(2) 0.47007(19) 0.14937(7) 0.0143(3) Uani d . 1 . .
C C4 0.1922(2) 0.40748(19) 0.04984(8) 0.0161(4) Uani d . 1 . .
C C5 0.3225(3) 0.5513(2) 0.06440(8) 0.0207(4) Uani d . 1 . .
H H5A 0.2630 0.6384 0.0390 0.025 Uiso calc R 1 . .
H H5B 0.4737 0.5349 0.0561 0.025 Uiso calc R 1 . .
C C6 0.0987(3) 0.3792(2) 0.20899(8) 0.0194(4) Uani d . 1 . .
H H6A 0.2353 0.3207 0.2110 0.023 Uiso calc R 1 . .
H H6B -0.0204 0.3041 0.2098 0.023 Uiso calc R 1 . .
C C7 0.1015(3) 0.4855(2) 0.26444(8) 0.0239(4) Uani d . 1 . .
H H7A 0.1098 0.4224 0.3020 0.029 Uiso calc R 1 . .
H H7B 0.2311 0.5517 0.2665 0.029 Uiso calc R 1 . .
C C8 -0.0989(3) 0.5870(2) 0.26138(8) 0.0230(4) Uani d . 1 . .
H H8A -0.2266 0.5217 0.2655 0.028 Uiso calc R 1 . .
H H8B -0.0852 0.6607 0.2959 0.028 Uiso calc R 1 . .
C C9 -0.1310(3) 0.6762(2) 0.20155(8) 0.0186(4) Uani d . 1 . .
H H9A -0.0129 0.7518 0.1999 0.022 Uiso calc R 1 . .
H H9B -0.2683 0.7338 0.1996 0.022 Uiso calc R 1 . .
C C10 -0.1346(2) 0.5672(2) 0.14669(8) 0.0159(4) Uani d . 1 . .
H H10A -0.2612 0.4983 0.1461 0.019 Uiso calc R 1 . .
H H10B -0.1486 0.6284 0.1086 0.019 Uiso calc R 1 . .
C C11 -0.0534(2) 0.22881(19) 0.08959(8) 0.0144(3) Uani d . 1 . .
C C12 -0.3796(3) 0.1143(2) 0.07570(9) 0.0214(4) Uani d . 1 . .
H H12 -0.5323 0.1194 0.0722 0.026 Uiso calc R 1 . .
C C13 -0.2817(3) -0.0280(2) 0.07264(8) 0.0215(4) Uani d . 1 . .
H H13 -0.3630 -0.1200 0.0658 0.026 Uiso calc R 1 . .
C C14 -0.0591(3) -0.0296(2) 0.08007(9) 0.0246(4) Uani d . 1 . .
H H14 0.0131 -0.1256 0.0785 0.030 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 S1 C2 . . 93.63(8) ?
C11 N1 C12 . . 115.20(15) ?
C11 N2 C14 . . 115.15(15) ?
C4 N3 C11 . . 118.58(14) ?
C4 N3 C2 . . 119.29(14) ?
C11 N3 C2 . . 122.06(13) ?
N3 C2 C10 . . 112.34(13) ?
N3 C2 C6 . . 111.29(14) ?
C10 C2 C6 . . 110.16(13) ?
N3 C2 S1 . . 102.80(10) ?
C10 C2 S1 . . 110.96(12) ?
C6 C2 S1 . . 109.06(11) ?
O1 C4 N3 . . 124.04(15) ?
O1 C4 C5 . . 123.77(15) ?
N3 C4 C5 . . 112.18(15) ?
C4 C5 S1 . . 107.29(12) ?
C4 C5 H5A . . 110.3 ?
S1 C5 H5A . . 110.3 ?
C4 C5 H5B . . 110.3 ?
S1 C5 H5B . . 110.3 ?
H5A C5 H5B . . 108.5 ?
C2 C6 C7 . . 111.52(15) ?
C2 C6 H6A . . 109.3 ?
C7 C6 H6A . . 109.3 ?
C2 C6 H6B . . 109.3 ?
C7 C6 H6B . . 109.3 ?
H6A C6 H6B . . 108.0 ?
C8 C7 C6 . . 111.59(15) ?
C8 C7 H7A . . 109.3 ?
C6 C7 H7A . . 109.3 ?
C8 C7 H7B . . 109.3 ?
C6 C7 H7B . . 109.3 ?
H7A C7 H7B . . 108.0 ?
C9 C8 C7 . . 111.57(14) ?
C9 C8 H8A . . 109.3 ?
C7 C8 H8A . . 109.3 ?
C9 C8 H8B . . 109.3 ?
C7 C8 H8B . . 109.3 ?
H8A C8 H8B . . 108.0 ?
C8 C9 C10 . . 111.08(15) ?
C8 C9 H9A . . 109.4 ?
C10 C9 H9A . . 109.4 ?
C8 C9 H9B . . 109.4 ?
C10 C9 H9B . . 109.4 ?
H9A C9 H9B . . 108.0 ?
C2 C10 C9 . . 111.29(13) ?
C2 C10 H10A . . 109.4 ?
C9 C10 H10A . . 109.4 ?
C2 C10 H10B . . 109.4 ?
C9 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108.0 ?
N2 C11 N1 . . 128.08(15) ?
N2 C11 N3 . . 115.10(13) ?
N1 C11 N3 . . 116.80(14) ?
N1 C12 C13 . . 122.23(16) ?
N1 C12 H12 . . 118.9 ?
C13 C12 H12 . . 118.9 ?
C12 C13 C14 . . 116.59(16) ?
C12 C13 H13 . . 121.7 ?
C14 C13 H13 . . 121.7 ?
N2 C14 C13 . . 122.69(17) ?
N2 C14 H14 . . 118.7 ?
C13 C14 H14 . . 118.7 ?
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
S1 C5 . 1.8004(19) ?
S1 C2 . 1.8494(16) ?
O1 C4 . 1.224(2) ?
N1 C11 . 1.330(2) ?
N1 C12 . 1.347(2) ?
N2 C11 . 1.328(2) ?
N2 C14 . 1.339(2) ?
N3 C4 . 1.363(2) ?
N3 C11 . 1.436(2) ?
N3 C2 . 1.480(2) ?
C2 C10 . 1.527(2) ?
C2 C6 . 1.528(2) ?
C4 C5 . 1.507(2) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.530(3) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.527(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.525(3) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.533(2) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C12 C13 . 1.382(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.384(2) ?
C13 H13 . 0.9500 ?
C14 H14 . 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
C10 H10a S1 1_455 0.99 2.80 3.4765(13) 126
C10 H10b O1 3_565 0.99 2.44 3.361(2) 155
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
C4 N3 C2 C10 . . . . 101.41(16) ?
C11 N3 C2 C10 . . . . -75.57(19) ?
C4 N3 C2 C6 . . . . -134.54(15) ?
C11 N3 C2 C6 . . . . 48.48(19) ?
C4 N3 C2 S1 . . . . -17.93(17) ?
C11 N3 C2 S1 . . . . 165.09(12) ?
C5 S1 C2 N3 . . . . 19.77(12) ?
C5 S1 C2 C10 . . . . -100.52(12) ?
C5 S1 C2 C6 . . . . 137.96(12) ?
C11 N3 C4 O1 . . . . 3.4(2) ?
C2 N3 C4 O1 . . . . -173.65(15) ?
C11 N3 C4 C5 . . . . -177.71(14) ?
C2 N3 C4 C5 . . . . 5.2(2) ?
O1 C4 C5 S1 . . . . -170.17(14) ?
N3 C4 C5 S1 . . . . 10.98(18) ?
C2 S1 C5 C4 . . . . -18.17(13) ?
N3 C2 C6 C7 . . . . 178.46(13) ?
C10 C2 C6 C7 . . . . -56.27(18) ?
S1 C2 C6 C7 . . . . 65.74(15) ?
C2 C6 C7 C8 . . . . 54.95(19) ?
C6 C7 C8 C9 . . . . -53.8(2) ?
C7 C8 C9 C10 . . . . 54.38(19) ?
N3 C2 C10 C9 . . . . -178.32(14) ?
C6 C2 C10 C9 . . . . 57.00(18) ?
S1 C2 C10 C9 . . . . -63.87(16) ?
C8 C9 C10 C2 . . . . -56.35(18) ?
C14 N2 C11 N1 . . . . 2.2(3) ?
C14 N2 C11 N3 . . . . -176.42(16) ?
C12 N1 C11 N2 . . . . -0.6(3) ?
C12 N1 C11 N3 . . . . 177.99(15) ?
C4 N3 C11 N2 . . . . 66.8(2) ?
C2 N3 C11 N2 . . . . -116.21(17) ?
C4 N3 C11 N1 . . . . -111.96(18) ?
C2 N3 C11 N1 . . . . 65.0(2) ?
C11 N1 C12 C13 . . . . -1.7(3) ?
N1 C12 C13 C14 . . . . 2.1(3) ?
C11 N2 C14 C13 . . . . -1.6(3) ?
C12 C13 C14 N2 . . . . -0.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743932
