#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:39:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180514 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/83/7218379.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7218379
loop_
_publ_author_name
'Dong, Hong Ru'
'Gao, Zhong Lian'
'Li, Rong Shan'
'Hu, Yi Ming'
'Dong, Heng Shan'
'Xie, Zhixiang'
_publ_section_title
;
 One-pot synthesis of 5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one
 derivatives
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA02714K
_journal_year                    2014
_chemical_formula_sum            'C12 H9 N3 O2 S'
_chemical_formula_weight         259.28
_chemical_name_systematic
;
2-(4-methoxyphenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.384(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.1942(13)
_cell_length_b                   13.4679(13)
_cell_length_c                   12.8940(12)
_cell_measurement_reflns_used    1276
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      2.37
_cell_volume                     2279.2(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5973
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.9231
_exptl_absorpt_correction_T_min  0.9082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00053(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0422
_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)+(0.0463P)²+0.9628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                1458
_reflns_number_total             2116
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra02714k2.cif
_cod_data_source_block           c2c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7218379
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.38204(17) 0.28634(18) -0.12129(19) 0.0447(6) Uani 1 1 d .
C2 C 0.39150(18) 0.22036(19) -0.2028(2) 0.0523(6) Uani 1 1 d .
H2 H 0.3960 0.2463 -0.2676 0.063 Uiso 1 1 calc R
C3 C 0.3941(2) 0.1214(2) -0.1886(2) 0.0604(7) Uani 1 1 d .
H3 H 0.3997 0.0827 -0.2457 0.073 Uiso 1 1 calc R
C4 C 0.38233(18) 0.13153(17) -0.0220(2) 0.0479(6) Uani 1 1 d .
C5 C 0.37143(16) 0.21914(16) 0.13815(18) 0.0420(6) Uani 1 1 d .
C6 C 0.36850(16) 0.24900(16) 0.24582(17) 0.0400(6) Uani 1 1 d .
C7 C 0.36165(17) 0.18019(17) 0.3231(2) 0.0463(6) Uani 1 1 d .
H7 H 0.3574 0.1128 0.3060 0.056 Uiso 1 1 calc R
C8 C 0.36108(18) 0.21069(17) 0.4240(2) 0.0474(6) Uani 1 1 d .
H8 H 0.3563 0.1639 0.4748 0.057 Uiso 1 1 calc R
C9 C 0.36764(17) 0.31075(17) 0.45135(19) 0.0442(6) Uani 1 1 d .
C10 C 0.37450(18) 0.38058(17) 0.3752(2) 0.0475(6) Uani 1 1 d .
H10 H 0.3786 0.4479 0.3924 0.057 Uiso 1 1 calc R
C11 C 0.37515(18) 0.34892(17) 0.2745(2) 0.0479(6) Uani 1 1 d .
H11 H 0.3802 0.3957 0.2239 0.057 Uiso 1 1 calc R
C12 C 0.3756(2) 0.43373(19) 0.5883(2) 0.0662(8) Uani 1 1 d .
H12A H 0.4391 0.4601 0.5902 0.099 Uiso 1 1 calc R
H12B H 0.3734 0.4381 0.6617 0.099 Uiso 1 1 calc R
H12C H 0.3203 0.4713 0.5362 0.099 Uiso 1 1 calc R
N1 N 0.38930(17) 0.07238(15) -0.09835(18) 0.0603(6) Uani 1 1 d .
N2 N 0.37830(13) 0.23275(13) -0.02779(15) 0.0401(5) Uani 1 1 d .
N3 N 0.37149(14) 0.28215(14) 0.06283(15) 0.0427(5) Uani 1 1 d .
O1 O 0.37659(14) 0.37608(13) -0.12341(14) 0.0590(5) Uani 1 1 d .
O2 O 0.36657(13) 0.33240(12) 0.55381(14) 0.0574(5) Uani 1 1 d .
S1 S 0.37725(5) 0.09414(4) 0.10407(5) 0.0559(3) Uani 1 1 d .
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
O1 C1 C2 129.1(2)
O1 C1 N2 120.2(2)
C2 C1 N2 110.7(2)
C3 C2 C1 121.7(2)
C3 C2 H2 119.2
C1 C2 H2 119.2
C2 C3 N1 126.1(2)
C2 C3 H3 117.0
N1 C3 H3 117.0
N1 C4 N2 125.7(2)
N1 C4 S1 125.19(19)
N2 C4 S1 109.06(17)
N3 C5 C6 122.9(2)
N3 C5 S1 115.48(17)
C6 C5 S1 121.64(17)
C11 C6 C7 118.1(2)
C11 C6 C5 119.8(2)
C7 C6 C5 122.2(2)
C8 C7 C6 120.6(2)
C8 C7 H7 119.7
C6 C7 H7 119.7
C7 C8 C9 120.6(2)
C7 C8 H8 119.7
C9 C8 H8 119.7
O2 C9 C8 115.5(2)
O2 C9 C10 124.8(2)
C8 C9 C10 119.6(2)
C11 C10 C9 119.1(2)
C11 C10 H10 120.4
C9 C10 H10 120.4
C10 C11 C6 122.0(2)
C10 C11 H11 119.0
C6 C11 H11 119.0
O2 C12 H12A 109.5
O2 C12 H12B 109.5
H12A C12 H12B 109.5
O2 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C4 N1 C3 113.2(2)
C4 N2 N3 116.74(19)
C4 N2 C1 122.6(2)
N3 N2 C1 120.67(18)
C5 N3 N2 109.92(18)
C9 O2 C12 118.41(19)
C4 S1 C5 88.78(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.211(3)
C1 C2 1.421(3)
C1 N2 1.423(3)
C2 C3 1.344(3)
C2 H2 0.9300
C3 N1 1.362(3)
C3 H3 0.9300
C4 N1 1.299(3)
C4 N2 1.365(3)
C4 S1 1.729(3)
C5 N3 1.290(3)
C5 C6 1.461(3)
C5 S1 1.750(2)
C6 C11 1.390(3)
C6 C7 1.391(3)
C7 C8 1.367(3)
C7 H7 0.9300
C8 C9 1.387(3)
C8 H8 0.9300
C9 O2 1.359(3)
C9 C10 1.389(3)
C10 C11 1.370(3)
C10 H10 0.9300
C11 H11 0.9300
C12 O2 1.426(3)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
N2 N3 1.380(2)
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 C1 C2 C3 -178.3(3)
N2 C1 C2 C3 1.2(3)
C1 C2 C3 N1 -0.6(4)
N3 C5 C6 C11 -5.9(3)
S1 C5 C6 C11 172.98(17)
N3 C5 C6 C7 175.6(2)
S1 C5 C6 C7 -5.4(3)
C11 C6 C7 C8 0.3(3)
C5 C6 C7 C8 178.7(2)
C6 C7 C8 C9 -0.2(4)
C7 C8 C9 O2 -179.9(2)
C7 C8 C9 C10 0.2(4)
O2 C9 C10 C11 179.8(2)
C8 C9 C10 C11 -0.3(4)
C9 C10 C11 C6 0.4(4)
C7 C6 C11 C10 -0.4(3)
C5 C6 C11 C10 -178.9(2)
N2 C4 N1 C3 1.0(4)
S1 C4 N1 C3 -178.69(19)
C2 C3 N1 C4 -0.5(4)
N1 C4 N2 N3 -179.7(2)
S1 C4 N2 N3 0.1(2)
N1 C4 N2 C1 -0.4(4)
S1 C4 N2 C1 179.34(16)
O1 C1 N2 C4 178.8(2)
C2 C1 N2 C4 -0.7(3)
O1 C1 N2 N3 -1.9(3)
C2 C1 N2 N3 178.53(18)
C6 C5 N3 N2 177.83(18)
S1 C5 N3 N2 -1.2(2)
C4 N2 N3 C5 0.7(3)
C1 N2 N3 C5 -178.59(19)
C8 C9 O2 C12 178.5(2)
C10 C9 O2 C12 -1.6(4)
N1 C4 S1 C5 179.2(2)
N2 C4 S1 C5 -0.57(17)
N3 C5 S1 C4 1.04(19)
C6 C5 S1 C4 -177.96(19)
