#------------------------------------------------------------------------------
#$Date: 2019-11-23 18:42:19 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234484 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/50/7125069.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_7125069
loop_
_publ_author_name
'Shemchuk, O.'
'Braga, D.'
'Grepioni, F.'
_publ_section_title
;
 Alloying barbituric and thiobarbituric acids: from solid solutions to a
 highly stable keto co-crystal form.
;
_journal_issue                   79
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11815
_journal_page_last               11818
_journal_paper_doi               10.1039/c6cc06615a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C8 H8 N4 O5.2 S0.8'
_chemical_formula_weight         269.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-08-10 deposited with the CCDC.
2016-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.490(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4662(13)
_cell_length_b                   12.9681(12)
_cell_length_c                   9.6819(11)
_cell_measurement_reflns_used    613
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.6320
_cell_measurement_theta_min      3.6150
_cell_volume                     1062.0(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2005)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4603
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        26.315
_diffrn_reflns_theta_max         29.353
_diffrn_reflns_theta_min         3.268
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             554
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.2337
_refine_ls_R_factor_gt           0.1059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1126P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2172
_refine_ls_wR_factor_ref         0.2839
_reflns_number_gt                962
_reflns_number_total             2431
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc06615a2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C8 H8 N4 O5.20 S0.80'
_cod_database_code               7125069
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.166(2) 0.5277(11) 0.0980(19) 0.089(6) Uani 0.6 1 d . . P A 1
S1A S 0.1844(11) 0.5562(6) 0.0708(9) 0.0423(15) Uani 0.4 1 d . . P A 1
O1B O -0.306(3) 0.2157(13) 0.627(2) 0.099(7) Uani 0.6 1 d . . P B 2
S1B S -0.2877(12) 0.1898(6) 0.5967(9) 0.0509(17) Uani 0.4 1 d . . P B 2
O3 O 0.1014(5) 0.1956(3) 0.1846(4) 0.0520(13) Uani 1 1 d . . . . .
N1 N 0.1384(5) 0.3644(3) 0.1451(5) 0.0396(13) Uani 1 1 d . . . . .
H1 H 0.1997 0.3490 0.0797 0.048 Uiso 1 1 calc R U . . .
C2 C 0.0831(7) 0.2851(4) 0.2191(6) 0.0381(15) Uani 1 1 d . . . . .
O5 O -0.4310(6) 0.5464(3) 0.6495(5) 0.0585(14) Uani 1 1 d . . . . .
O4 O -0.6525(5) 0.2960(4) 0.9388(5) 0.0617(14) Uani 1 1 d . . . . .
O2 O -0.1616(5) 0.4498(3) 0.4286(4) 0.0565(13) Uani 1 1 d . . . . .
C3 C -0.0629(7) 0.4217(4) 0.3519(6) 0.0397(15) Uani 1 1 d . . . . .
N3 N -0.3761(6) 0.3773(4) 0.6323(5) 0.0479(15) Uani 1 1 d . . . . .
H3 H -0.3154 0.3904 0.5655 0.057 Uiso 1 1 calc R U . . .
N2 N 0.0057(5) 0.4900(3) 0.2647(5) 0.0418(13) Uani 1 1 d . . . . .
H2 H -0.0173 0.5541 0.2747 0.050 Uiso 1 1 calc R U . . .
N4 N -0.4857(6) 0.2553(3) 0.7762(5) 0.0484(14) Uani 1 1 d . . . . .
H4 H -0.4935 0.1917 0.8000 0.058 Uiso 1 1 calc R U . . .
C1 C 0.1074(7) 0.4662(4) 0.1631(6) 0.0383(15) Uani 1 1 d . . . . .
C4 C 0.0025(7) 0.3144(4) 0.3473(6) 0.0432(16) Uani 1 1 d . . . . .
H4A H 0.0772 0.3058 0.4253 0.052 Uiso 1 1 calc R U . . .
H4B H -0.0835 0.2663 0.3597 0.052 Uiso 1 1 calc R U . . .
C6 C -0.4534(7) 0.4590(4) 0.6876(7) 0.0450(16) Uani 1 1 d . . . . .
C8 C -0.5741(7) 0.3247(5) 0.8451(6) 0.0449(16) Uani 1 1 d . . . . .
C5 C -0.3859(7) 0.2773(5) 0.6729(6) 0.0415(16) Uani 1 1 d . . . . .
C7 C -0.5704(8) 0.4317(5) 0.7934(7) 0.058(2) Uani 1 1 d . . . . .
H7A H -0.5511 0.4767 0.8724 0.069 Uiso 1 1 calc R U . . .
H7B H -0.6750 0.4480 0.7547 0.069 Uiso 1 1 calc R U . . .
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
C2 N1 C1 126.8(5)
C2 N1 H1 116.6
C1 N1 H1 116.6
O3 C2 N1 122.0(5)
O3 C2 C4 122.6(5)
N1 C2 C4 115.4(5)
O2 C3 N2 120.7(5)
O2 C3 C4 124.6(5)
N2 C3 C4 114.5(5)
C5 N3 C6 126.2(5)
C5 N3 H3 116.9
C6 N3 H3 116.9
C3 N2 C1 126.4(5)
C3 N2 H2 116.8
C1 N2 H2 116.8
C8 N4 C5 126.2(5)
C8 N4 H4 116.9
C5 N4 H4 116.9
O1A C1 N1 121.2(10)
O1A C1 N2 122.6(11)
N1 C1 N2 116.2(5)
O1A C1 S1A 2.1(12)
N1 C1 S1A 122.9(5)
N2 C1 S1A 120.8(5)
C2 C4 C3 116.3(5)
C2 C4 H4A 108.2
C3 C4 H4A 108.2
C2 C4 H4B 108.2
C3 C4 H4B 108.2
H4A C4 H4B 107.4
O5 C6 N3 121.5(5)
O5 C6 C7 123.2(5)
N3 C6 C7 115.2(5)
O4 C8 N4 119.8(6)
O4 C8 C7 124.4(6)
N4 C8 C7 115.7(5)
O1B C5 N3 120.5(11)
O1B C5 N4 122.0(11)
N3 C5 N4 117.3(5)
O1B C5 S1B 5.8(15)
N3 C5 S1B 120.2(5)
N4 C5 S1B 122.5(5)
C8 C7 C6 118.6(5)
C8 C7 H7A 107.7
C6 C7 H7A 107.7
C8 C7 H7B 107.7
C6 C7 H7B 107.7
H7A C7 H7B 107.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1A C1 1.142(13)
S1A C1 1.623(8)
O1B C5 1.149(14)
S1B C5 1.605(9)
O3 C2 1.219(6)
N1 C2 1.349(6)
N1 C1 1.358(7)
N1 H1 0.8600
C2 C4 1.492(7)
O5 C6 1.208(7)
O4 C8 1.206(6)
O2 C3 1.199(6)
C3 N2 1.369(6)
C3 C4 1.499(8)
N3 C5 1.358(7)
N3 C6 1.367(7)
N3 H3 0.8600
N2 C1 1.371(6)
N2 H2 0.8600
N4 C8 1.363(7)
N4 C5 1.368(7)
N4 H4 0.8600
C4 H4A 0.9700
C4 H4B 0.9700
C6 C7 1.498(8)
C8 C7 1.476(8)
C7 H7A 0.9700
C7 H7B 0.9700
