#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:39:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180514 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/83/7218380.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_7218380
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            'C11 H6 Cl N3 O S'
_chemical_formula_weight         263.70
_chemical_name_systematic
;
?
;
_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                90.00
_cell_angle_beta                 98.505(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.838(4)
_cell_length_b                   4.9244(19)
_cell_length_c                   20.011(7)
_cell_measurement_reflns_used    2371
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      2.29
_cell_volume                     1056.3(7)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5348
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  0.8499
_exptl_absorpt_correction_T_min  0.8205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0330
_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)+(0.0455P)²+0.3450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0902
_reflns_number_gt                1745
_reflns_number_total             2061
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra02714k2.cif
_cod_data_source_block           p21n
_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      P2(1)/n
_cod_database_code               7218380
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_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 0.91753(16) 1.0176(4) 0.15236(9) 0.0391(4) Uani 1 1 d .
C2 C 1.02215(17) 0.9304(4) 0.19495(9) 0.0461(5) Uani 1 1 d .
H2 H 1.0385 0.9957 0.2390 0.055 Uiso 1 1 calc R
C3 C 1.10134(18) 0.7485(4) 0.17230(11) 0.0493(5) Uani 1 1 d .
H3 H 1.1712 0.6883 0.2011 0.059 Uiso 1 1 calc R
C4 C 1.07830(18) 0.6536(5) 0.10707(10) 0.0535(5) Uani 1 1 d .
H4 H 1.1319 0.5286 0.0917 0.064 Uiso 1 1 calc R
C5 C 0.97525(19) 0.7454(4) 0.06483(10) 0.0483(5) Uani 1 1 d .
H5 H 0.9609 0.6827 0.0205 0.058 Uiso 1 1 calc R
C6 C 0.89174(15) 0.9286(4) 0.08606(8) 0.0357(4) Uani 1 1 d .
C7 C 0.78510(15) 1.0098(4) 0.03592(8) 0.0344(4) Uani 1 1 d .
C8 C 0.60694(16) 1.2039(4) -0.03510(9) 0.0367(4) Uani 1 1 d .
C9 C 0.47030(19) 1.2401(4) -0.12908(10) 0.0500(5) Uani 1 1 d .
H9 H 0.4009 1.3250 -0.1531 0.060 Uiso 1 1 calc R
C10 C 0.52210(17) 1.0393(4) -0.16020(9) 0.0447(5) Uani 1 1 d .
H10 H 0.4883 0.9939 -0.2042 0.054 Uiso 1 1 calc R
C11 C 0.62754(16) 0.8928(4) -0.12784(8) 0.0407(4) Uani 1 1 d .
Cl1 Cl 0.81942(5) 1.24001(12) 0.18661(3) 0.0615(2) Uani 1 1 d .
N1 N 0.76561(13) 0.8835(3) -0.02121(7) 0.0380(3) Uani 1 1 d .
N2 N 0.66547(12) 0.9951(3) -0.06152(6) 0.0356(3) Uani 1 1 d .
N3 N 0.50985(15) 1.3313(4) -0.06552(8) 0.0486(4) Uani 1 1 d .
O1 O 0.68243(13) 0.7074(3) -0.14954(7) 0.0579(4) Uani 1 1 d .
S1 S 0.68161(4) 1.27138(9) 0.04545(2) 0.04176(16) 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 121.53(17)
C2 C1 Cl1 116.54(14)
C6 C1 Cl1 121.92(13)
C3 C2 C1 119.89(18)
C3 C2 H2 120.1
C1 C2 H2 120.1
C2 C3 C4 120.28(18)
C2 C3 H3 119.9
C4 C3 H3 119.9
C5 C4 C3 119.33(19)
C5 C4 H4 120.3
C3 C4 H4 120.3
C4 C5 C6 122.21(18)
C4 C5 H5 118.9
C6 C5 H5 118.9
C1 C6 C5 116.76(16)
C1 C6 C7 126.48(16)
C5 C6 C7 116.76(16)
N1 C7 C6 118.86(15)
N1 C7 S1 115.52(12)
C6 C7 S1 125.60(13)
N3 C8 N2 125.28(16)
N3 C8 S1 125.55(14)
N2 C8 S1 109.17(12)
C10 C9 N3 125.85(17)
C10 C9 H9 117.1
N3 C9 H9 117.1
C9 C10 C11 121.84(17)
C9 C10 H10 119.1
C11 C10 H10 119.1
O1 C11 N2 120.97(16)
O1 C11 C10 128.74(17)
N2 C11 C10 110.29(15)
C7 N1 N2 109.88(14)
C8 N2 N1 116.80(13)
C8 N2 C11 123.03(14)
N1 N2 C11 120.16(14)
C8 N3 C9 113.69(16)
C8 S1 C7 88.62(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.382(2)
C1 C6 1.386(2)
C1 Cl1 1.7365(19)
C2 C3 1.364(3)
C2 H2 0.9300
C3 C4 1.374(3)
C3 H3 0.9300
C4 C5 1.374(3)
C4 H4 0.9300
C5 C6 1.388(3)
C5 H5 0.9300
C6 C7 1.470(2)
C7 N1 1.291(2)
C7 S1 1.7370(17)
C8 N3 1.297(2)
C8 N2 1.356(2)
C8 S1 1.7255(18)
C9 C10 1.336(3)
C9 N3 1.357(3)
C9 H9 0.9300
C10 C11 1.424(2)
C10 H10 0.9300
C11 O1 1.205(2)
C11 N2 1.422(2)
N1 N2 1.3681(18)
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
C6 C1 C2 C3 -1.3(3)
Cl1 C1 C2 C3 177.80(16)
C1 C2 C3 C4 0.7(3)
C2 C3 C4 C5 0.5(3)
C3 C4 C5 C6 -1.1(4)
C2 C1 C6 C5 0.7(3)
Cl1 C1 C6 C5 -178.34(15)
C2 C1 C6 C7 -178.96(17)
Cl1 C1 C6 C7 2.0(3)
C4 C5 C6 C1 0.5(3)
C4 C5 C6 C7 -179.81(19)
C1 C6 C7 N1 -171.48(17)
C5 C6 C7 N1 8.8(3)
C1 C6 C7 S1 10.0(3)
C5 C6 C7 S1 -169.66(15)
N3 C9 C10 C11 0.9(4)
C9 C10 C11 O1 179.3(2)
C9 C10 C11 N2 -0.7(3)
C6 C7 N1 N2 -177.77(14)
S1 C7 N1 N2 0.86(19)
N3 C8 N2 N1 -179.02(18)
S1 C8 N2 N1 0.63(19)
N3 C8 N2 C11 1.3(3)
S1 C8 N2 C11 -179.04(14)
C7 N1 N2 C8 -1.0(2)
C7 N1 N2 C11 178.71(15)
O1 C11 N2 C8 179.70(18)
C10 C11 N2 C8 -0.3(3)
O1 C11 N2 N1 0.0(3)
C10 C11 N2 N1 -179.94(15)
N2 C8 N3 C9 -1.2(3)
S1 C8 N3 C9 179.25(15)
C10 C9 N3 C8 0.1(3)
N3 C8 S1 C7 179.54(19)
N2 C8 S1 C7 -0.11(13)
N1 C7 S1 C8 -0.45(15)
C6 C7 S1 C8 178.07(16)
