#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/17/2211714.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_2211714
loop_
_publ_author_name
'da Silva, Luiz Everson'
'Joussef, Antonio Carlos'
'Foro, Sabine'
_publ_section_title
;
 2-Ethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one
;
_journal_coeditor_code           AT2191
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o412
_journal_page_last               o413
_journal_paper_doi               10.1107/S1600536806054584
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C7 H7 N3 O S'
_chemical_formula_moiety         'C7 H7 N3 O S'
_chemical_formula_sum            'C7 H7 N3 O S'
_chemical_formula_weight         181.22
_chemical_name_systematic
;
2-Ethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   32.347(5)
_cell_length_b                   32.347(5)
_cell_length_c                   4.0784(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      22.44
_cell_measurement_theta_min      2.72
_cell_volume                     3695.6(10)
_computing_cell_refinement       CAD-4-P
_computing_data_collection       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            2610
_diffrn_reflns_theta_full        67.02
_diffrn_reflns_theta_max         67.02
_diffrn_reflns_theta_min         2.73
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.130
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1692
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0354P)²+5.1533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                1300
_reflns_number_total             1461
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2191.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2211714
_cod_database_fobs_code          2211714
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
C C1 0.55518(7) 0.05415(7) 0.7714(6) 0.0447(5) Uani d . 1
C C2 0.58484(9) 0.00476(8) 0.7603(7) 0.0583(6) Uani d . 1
H H2 0.5817 -0.0245 0.7014 0.070 Uiso calc R 1
C C3 0.62488(8) 0.03589(8) 0.9224(7) 0.0550(6) Uani d . 1
H H3 0.6479 0.0274 0.9664 0.066 Uiso calc R 1
C C4 0.63301(7) 0.08141(8) 1.0282(6) 0.0503(5) Uani d . 1
C C5 0.55557(7) 0.12711(7) 0.9159(5) 0.0421(5) Uani d . 1
C C6 0.54357(8) 0.16538(8) 0.9765(6) 0.0503(5) Uani d . 1
H H6A 0.5172 0.1537 1.1302 0.060 Uiso calc R 1
H H6B 0.5332 0.1727 0.7724 0.060 Uiso calc R 1
C C7 0.58523(9) 0.21070(9) 1.1117(7) 0.0655(7) Uani d . 1
H H7A 0.6113 0.2228 0.9590 0.079 Uiso calc R 1
H H7B 0.5951 0.2039 1.3169 0.079 Uiso calc R 1
H H7C 0.5757 0.2341 1.1450 0.079 Uiso calc R 1
N N1 0.54876(7) 0.01286(7) 0.6765(6) 0.0566(5) Uani d . 1
N N2 0.59440(6) 0.08808(6) 0.9367(4) 0.0431(4) Uani d . 1
N N3 0.59451(6) 0.12968(6) 1.0188(5) 0.0448(4) Uani d . 1
O O1 0.66693(6) 0.11216(6) 1.1798(5) 0.0680(5) Uani d . 1
S S1 0.515621(18) 0.074899(19) 0.71057(15) 0.0490(2) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0367(10) 0.0382(10) 0.0556(13) 0.0160(9) 0.0008(9) 0.0013(9)
C2 0.0545(13) 0.0415(12) 0.0815(18) 0.0259(11) 0.0013(12) -0.0053(11)
C3 0.0464(12) 0.0462(12) 0.0777(17) 0.0272(10) 0.0009(11) 0.0008(11)
C4 0.0380(11) 0.0441(12) 0.0693(15) 0.0209(10) -0.0012(10) 0.0030(10)
C5 0.0375(10) 0.0393(10) 0.0472(12) 0.0174(8) 0.0042(8) 0.0018(9)
C6 0.0481(12) 0.0525(12) 0.0578(14) 0.0307(10) 0.0016(10) -0.0029(10)
C7 0.0662(16) 0.0551(14) 0.0824(18) 0.0357(13) -0.0059(13) -0.0175(13)
N1 0.0492(11) 0.0407(10) 0.0789(14) 0.0216(8) -0.0088(10) -0.0109(9)
N2 0.0349(8) 0.0343(8) 0.0580(11) 0.0158(7) 0.0004(7) -0.0005(7)
N3 0.0396(9) 0.0371(9) 0.0577(11) 0.0192(7) -0.0008(8) -0.0035(8)
O1 0.0478(9) 0.0517(9) 0.1054(15) 0.0255(8) -0.0224(9) -0.0128(9)
S1 0.0377(3) 0.0418(3) 0.0657(4) 0.0186(2) -0.0061(2) -0.0042(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 -1 1
-2 -2 1
-2 0 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 N2 125.20(19)
N1 C1 S1 125.69(17)
N2 C1 S1 109.12(14)
C3 C2 N1 125.0(2)
C3 C2 H2 117.5
N1 C2 H2 117.5
C2 C3 C4 122.0(2)
C2 C3 H3 119.0
C4 C3 H3 119.0
O1 C4 N2 120.7(2)
O1 C4 C3 128.5(2)
N2 C4 C3 110.81(19)
N3 C5 C6 122.91(19)
N3 C5 S1 116.45(15)
C6 C5 S1 120.60(16)
C5 C6 C7 112.89(19)
C5 C6 H6A 109.0
C7 C6 H6A 109.0
C5 C6 H6B 109.0
C7 C6 H6B 109.0
H6A C6 H6B 107.8
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C1 N1 C2 114.2(2)
C1 N2 N3 116.66(16)
C1 N2 C4 122.71(17)
N3 N2 C4 120.61(17)
C5 N3 N2 109.31(17)
C1 S1 C5 88.46(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.304(3)
C1 N2 1.370(3)
C1 S1 1.734(2)
C2 C3 1.351(3)
C2 N1 1.362(3)
C2 H2 0.9300
C3 C4 1.427(3)
C3 H3 0.9300
C4 O1 1.218(3)
C4 N2 1.419(3)
C5 N3 1.290(3)
C5 C6 1.492(3)
C5 S1 1.744(2)
C6 C7 1.514(3)
C6 H6A 0.9700
C6 H6B 0.9700
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
N2 N3 1.385(2)
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
C6 H6A O1 17_557 0.97 2.49 3.450(3) 171.5
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
N1 C2 C3 C4 0.9(4)
C2 C3 C4 O1 178.7(3)
C2 C3 C4 N2 -0.5(3)
N3 C5 C6 C7 10.9(3)
S1 C5 C6 C7 -171.47(18)
N2 C1 N1 C2 1.1(4)
S1 C1 N1 C2 -178.74(19)
C3 C2 N1 C1 -1.1(4)
N1 C1 N2 N3 -179.5(2)
S1 C1 N2 N3 0.3(2)
N1 C1 N2 C4 -0.8(3)
S1 C1 N2 C4 178.99(17)
O1 C4 N2 C1 -178.8(2)
C3 C4 N2 C1 0.5(3)
O1 C4 N2 N3 -0.1(3)
C3 C4 N2 N3 179.13(19)
C6 C5 N3 N2 177.48(19)
S1 C5 N3 N2 -0.3(2)
C1 N2 N3 C5 0.0(3)
C4 N2 N3 C5 -178.76(19)
N1 C1 S1 C5 179.5(2)
N2 C1 S1 C5 -0.34(16)
N3 C5 S1 C1 0.37(18)
C6 C5 S1 C1 -177.44(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125729
