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#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/92/1529238.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_1529238
loop_
_publ_author_name
'Golovnev, Nikolay'
'Molokeev, Maxim'
'Tarasova, Ludmila'
'Atuchin, Victor'
'Vladimirova, Natalya'
_publ_section_title
;
 The 5-(isopropylidene)-2-thiobarbituric acid: Preparation, crystal
 structure, thermal stability and IR-characterization
;
_journal_issue                   0
_journal_name_full               'Journal of Molecular Structure'
_journal_page_first              216
_journal_paper_doi               10.1016/j.molstruc.2014.04.024
_journal_volume                  1068
_journal_year                    2014
_chemical_formula_moiety         'C7 H8 N2 O2 S'
_chemical_formula_sum            'C7 H8 N2 O2 S'
_chemical_formula_weight         184.21
_chemical_name_systematic
; 
5-(isopropylidene)-2-thiobarbituric acid  
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 105.388(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8268(19)
_cell_length_b                   12.044(3)
_cell_length_c                   8.0998(19)
_cell_measurement_temperature    296(2)
_cell_volume                     830.2(3)
_computing_cell_refinement       'APEX2 (Bruker, 2003-2008)'
_computing_data_collection       'APEX2 (Bruker, 2003-2008)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2005)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0603
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4008
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.65
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1. Bruker AXS Inc., Madison, Wisconsin, USA, 2004
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         4008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1611
_refine_ls_R_factor_gt           0.0865
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0667P)²+1.0647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1821
_refine_ls_wR_factor_ref         0.2237
_reflns_number_gt                2121
_reflns_number_total             4008
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            HTBA_AC.cif
_cod_data_source_block           a
_cod_original_sg_symbol_Hall
;
-P 2ybc
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1529238
_cod_database_fobs_code          1529238
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.73837(12) 0.12729(8) 1.02215(13) 0.0524(3) Uani 1 1 d . . .
O1 O 0.3618(3) -0.06941(18) 0.5725(3) 0.0527(8) Uani 1 1 d . . .
O2 O 0.3379(3) 0.32484(18) 0.5981(4) 0.0564(8) Uani 1 1 d . . .
N1 N 0.5149(3) 0.2222(2) 0.7817(4) 0.0393(7) Uani 1 1 d . . .
H1 H 0.5569 0.2833 0.8263 0.047 Uiso 1 1 calc R . .
N3 N 0.5193(3) 0.0320(2) 0.7776(4) 0.0387(7) Uani 1 1 d . . .
H3 H 0.5595 -0.0293 0.8238 0.050 Uiso 1 1 calc R . .
C4 C 0.3951(4) 0.0233(3) 0.6332(4) 0.0359(8) Uani 1 1 d . . .
C5 C 0.3131(4) 0.1270(3) 0.5639(4) 0.0337(7) Uani 1 1 d . . .
C6 C 0.3843(4) 0.2313(3) 0.6444(4) 0.0371(8) Uani 1 1 d . . .
C2 C 0.5847(4) 0.1269(3) 0.8544(4) 0.0354(7) Uani 1 1 d . . .
C7 C 0.1790(4) 0.1269(3) 0.4331(4) 0.0397(8) Uani 1 1 d . . .
C8 C 0.1067(4) 0.0249(3) 0.3409(5) 0.0578(11) Uani 1 1 d . . .
H8A H -0.0011 0.0395 0.2823 0.069 Uiso 1 1 calc R . .
H8B H 0.1118 -0.0342 0.4217 0.069 Uiso 1 1 calc R . .
H8C H 0.1628 0.0038 0.2592 0.069 Uiso 1 1 calc R . .
C9 C 0.0869(5) 0.2293(3) 0.3675(5) 0.0557(11) Uani 1 1 d . . .
H9A H 0.0673 0.2699 0.4617 0.067 Uiso 1 1 calc R . .
H9B H -0.0114 0.2088 0.2894 0.067 Uiso 1 1 calc R . .
H9C H 0.1455 0.2749 0.3092 0.067 Uiso 1 1 calc R . .
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'
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'
H H 0.0000 0.0000 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 C6 127.1(3) . .
C2 N1 H1 116.5 . .
C6 N1 H1 116.5 . .
C2 N3 C4 126.8(3) . .
C2 N3 H3 116.6 . .
C4 N3 H3 116.6 . .
O1 C4 N3 117.5(3) . .
O1 C4 C5 125.3(3) . .
N3 C4 C5 117.2(3) . .
C7 C5 C6 121.6(3) . .
C7 C5 C4 122.1(3) . .
C6 C5 C4 116.3(3) . .
O2 C6 N1 117.5(3) . .
O2 C6 C5 125.4(3) . .
N1 C6 C5 117.1(3) . .
N3 C2 N1 115.1(3) . .
N3 C2 S 122.6(2) . .
N1 C2 S 122.3(3) . .
C5 C7 C8 123.9(3) . .
C5 C7 C9 123.6(3) . .
C8 C7 C9 112.4(3) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S C2 1.645(3) .
O1 C4 1.224(4) .
O2 C6 1.223(4) .
N1 C2 1.360(4) .
N1 C6 1.377(4) .
N1 H1 0.8600 .
N3 C2 1.355(4) .
N3 C4 1.379(4) .
N3 H3 0.8600 .
C4 C5 1.478(4) .
C5 C7 1.364(4) .
C5 C6 1.476(4) .
C7 C8 1.490(5) .
C7 C9 1.495(5) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.01 2.863(3) 176 2_656
N3 H3 O2 0.86 2.00 2.856(4) 172 2_646
C9 H9B S 0.96 2.83 3.773(4) 168 1_454
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C2 N3 C4 O1 173.0(3) . . . .
C2 N3 C4 C5 -6.9(5) . . . .
O1 C4 C5 C7 7.2(6) . . . .
N3 C4 C5 C7 -172.9(3) . . . .
O1 C4 C5 C6 -172.9(3) . . . .
N3 C4 C5 C6 7.0(5) . . . .
C2 N1 C6 O2 179.4(3) . . . .
C2 N1 C6 C5 -1.4(5) . . . .
C7 C5 C6 O2 -4.3(6) . . . .
C4 C5 C6 O2 175.8(4) . . . .
C7 C5 C6 N1 176.6(3) . . . .
C4 C5 C6 N1 -3.4(5) . . . .
C4 N3 C2 N1 2.2(5) . . . .
C4 N3 C2 S -177.2(3) . . . .
C6 N1 C2 N3 2.3(5) . . . .
C6 N1 C2 S -178.3(3) . . . .
C6 C5 C7 C8 176.6(3) . . . .
C4 C5 C7 C8 -3.5(6) . . . .
C6 C5 C7 C9 -4.2(6) . . . .
C4 C5 C7 C9 175.7(3) . . . .
