#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/95/2009565.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_2009565
loop_
_publ_author_name
'Linden, Anthony'
'Heimgartner, Heinz'
'García Trimiño, Maria Isabel'
'Macías Cabrera, Arturo'
_publ_section_title
;
 5-Nitropyrimidines from 3,3-diamino(2-nitro)thioacrylamides. Structure
 of 6-(2-furfurylamino)-2-(2-furyl)-4-methylthio-5-nitropyrimidine
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              421
_journal_page_last               424
_journal_paper_doi               10.1107/S0108270193008558
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C14 H12 N4 O4 S'
_chemical_formula_sum            'C14 H12 N4 O4 S'
_chemical_formula_weight         332.33
_chemical_name_systematic
' 6-(2-furfurylamino)-2-(2-furyl)-4-methylthio-5-nitropyrimidine'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                95.23(3)
_cell_angle_beta                 96.84(3)
_cell_angle_gamma                93.74(2)
_cell_formula_units_Z            2
_cell_length_a                   11.099(3)
_cell_length_b                   15.200(4)
_cell_length_c                   4.416(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    173
_cell_measurement_theta_max      20
_cell_measurement_theta_min      15
_cell_volume                     734.4(4)
_computing_cell_refinement       ' MSC/AFC'
_computing_data_collection
' MSC/AFC (Molecular Structure Corporation, 1991)'
_computing_data_reduction
' TEXSAN: PROCESS (Molecular Structure Corporation, 1985)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
' TEXSAN: FINISH (Molecular Structure Corporation, 1985)'
_computing_structure_refinement
' TEXSAN: LS (Molecular Structure Corporation, 1985)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173
_diffrn_measurement_device       'Rigaku AFC-5R diffractometer'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3546
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         5
_diffrn_standards_decay_%        insignificant
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  1.192
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_type   'empirical (DIFABS: Walker & Stuart, 1983)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.31
_refine_ls_extinction_coef       'g = 2(2)E7'
_refine_ls_extinction_method     'Zachariasen (1963)'
_refine_ls_goodness_of_fit_obs   1.640
_refine_ls_hydrogen_treatment    'H atoms refined isotropically'
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_obs          0.0456
_refine_ls_shift/esd_max         0.0005
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fₒ) + (0.005Fₒ)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0486
_refine_ls_wR_factor_obs         0.0427
_reflns_number_observed          2134
_reflns_number_total             3374
_reflns_observed_criterion       'I > 3\s(I)'
_cod_data_source_file            sh1074.cif
_cod_data_source_block           HG9304
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/[\s^2^(F~o~) +
(0.005F~o~)^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1/[\s^2^(F~o~) + (0.005F~o~)^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        734.5(4)
_cod_database_code               2009565
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_type_symbol
S 0.92094(7) 0.92811(5) 1.2329(2) 0.0256(2) Uani ? ? S
O(1) 1.0883(2) 0.8169(2) 1.2209(5) 0.0358(8) Uani ? ? O
O(2) 1.1074(2) 0.7036(2) 0.8978(5) 0.0397(8) Uani ? ? O
O(3) 0.8290(2) 0.45310(10) 0.5065(5) 0.0326(8) Uani ? ? O
O(4) 0.5294(2) 0.7487(2) 0.1884(6) 0.0477(9) Uani ? ? O
N(1) 0.7618(2) 0.7246(2) 0.4556(5) 0.0235(8) Uani ? ? N
N(3) 0.7527(2) 0.8566(2) 0.7966(6) 0.0250(8) Uani ? ? N
N(5) 1.0478(2) 0.7652(2) 0.9927(6) 0.0273(9) Uani ? ? N
N(6) 0.9292(2) 0.6447(2) 0.4713(6) 0.0264(9) Uani ? ? N
C(1) 0.8026(3) 1.0032(2) 1.2092(9) 0.0340(10) Uani ? ? C
C(2) 0.7075(3) 0.7945(2) 0.5652(7) 0.0233(9) Uani ? ? C
C(4) 0.8630(3) 0.8470(2) 0.9349(6) 0.0214(9) Uani ? ? C
C(5) 0.9302(3) 0.7749(2) 0.8418(7) 0.0212(9) Uani ? ? C
C(6) 0.8752(3) 0.7144(2) 0.5895(7) 0.0234(9) Uani ? ? C
C(7) 0.8665(3) 0.5803(2) 0.2254(7) 0.0270(10) Uani ? ? C
C(8) 0.7797(3) 0.5153(2) 0.3310(7) 0.0249(9) Uani ? ? C
C(9) 0.6585(3) 0.5006(2) 0.2880(8) 0.0370(10) Uani ? ? C
C(10) 0.6275(3) 0.4248(2) 0.4381(9) 0.0400(10) Uani ? ? C
C(11) 0.7329(3) 0.3988(2) 0.5669(9) 0.0380(10) Uani ? ? C
C(12) 0.5861(3) 0.8074(2) 0.4235(7) 0.0270(10) Uani ? ? C
C(13) 0.5153(3) 0.8723(2) 0.4972(8) 0.0370(10) Uani ? ? C
C(14) 0.4042(4) 0.8520(4) 0.2980(10) 0.061(2) Uani ? ? C
C(15) 0.4157(4) 0.7800(3) 0.1160(10) 0.056(2) Uani ? ? C
H(6) 1.006(3) 0.639(2) 0.566(8) 0.040(10) Uiso ? ? H
H(9) 0.612(3) 0.532(3) 0.178(9) 0.060(10) Uiso ? ? H
H(10) 0.548(3) 0.399(2) 0.445(8) 0.050(10) Uiso ? ? H
H(11) 0.758(3) 0.351(2) 0.689(9) 0.060(10) Uiso ? ? H
H(13) 0.535 0.921 0.649 0.080(10) Uiso calc C(11) H
H(14) 0.340(4) 0.884(3) 0.290(10) 0.10(2) Uiso ? ? H
H(15) 0.363(4) 0.751(3) -0.050(10) 0.090(10) Uiso ? ? H
H(71) 0.821(3) 0.613(2) 0.073(7) 0.034(9) Uiso ? ? H
H(72) 0.929(3) 0.551(2) 0.136(7) 0.037(9) Uiso ? ? H
H(101) 0.796(4) 1.029(3) 1.010(10) 0.080(10) Uiso ? ? H
H(102) 0.727(3) 0.976(2) 1.244(8) 0.050(10) Uiso ? ? H
H(103) 0.824(3) 1.053(2) 1.356(8) 0.060(10) Uiso ? ? H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.003 0.002 International_Tables_for_X-ray_Crystallography_(1974,_Vol._4)
H 0.000 0.000 International_Tables_for_X-ray_Crystallography_(1974,_Vol._4)
N 0.006 0.003 International_Tables_for_X-ray_Crystallography_(1974,_Vol._4)
O 0.011 0.006 International_Tables_for_X-ray_Crystallography_(1974,_Vol._4)
S 0.125 0.123 International_Tables_for_X-ray_Crystallography_(1974,_Vol._4)
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 -3 1
-2 -2 1
-2 -4 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(1) S C(4) 100.5(2) yes
C(8) O(3) C(11) 106.3(3) yes
C(12) O(4) C(15) 104.9(3) yes
C(2) N(1) C(6) 116.7(3) yes
C(2) N(3) C(4) 116.7(3) yes
O(1) N(5) O(2) 121.4(3) yes
O(1) N(5) C(5) 119.1(3) yes
O(2) N(5) C(5) 119.5(3) yes
C(6) N(6) C(7) 122.5(3) yes
N(1) C(2) N(3) 127.6(3) yes
N(1) C(2) C(12) 117.8(3) yes
N(3) C(2) C(12) 114.6(3) yes
S C(4) N(3) 116.3(2) yes
S C(4) C(5) 122.4(2) yes
N(3) C(4) C(5) 121.3(3) yes
N(5) C(5) C(4) 120.7(3) yes
N(5) C(5) C(6) 121.9(3) yes
C(4) C(5) C(6) 117.4(3) yes
N(1) C(6) N(6) 115.7(3) yes
N(1) C(6) C(5) 120.3(3) yes
N(6) C(6) C(5) 124.0(3) yes
N(6) C(7) C(8) 113.9(3) yes
O(3) C(8) C(7) 116.6(3) yes
O(3) C(8) C(9) 109.3(3) yes
C(7) C(8) C(9) 134.0(3) yes
C(8) C(9) C(10) 107.8(3) yes
C(9) C(10) C(11) 106.0(3) yes
O(3) C(11) C(10) 110.6(3) yes
O(4) C(12) C(2) 120.5(3) yes
O(4) C(12) C(13) 111.8(3) yes
C(2) C(12) C(13) 127.7(3) yes
C(12) C(13) C(14) 105.0(3) yes
C(13) C(14) C(15) 108.2(4) yes
O(4) C(15) C(14) 110.1(4) yes
C(6) N(6) H(6) 114.(2) no
C(7) N(6) H(6) 124.(2) no
S C(1) H(101) 111.(2) no
S C(1) H(102) 112.(2) no
S C(1) H(103) 110.(2) no
H(101) C(1) H(102) 111.(3) no
H(101) C(1) H(103) 104.(3) no
H(102) C(1) H(103) 109.(3) no
N(6) C(7) H(71) 108.(2) no
N(6) C(7) H(72) 106.(2) no
C(8) C(7) H(71) 108.(2) no
C(8) C(7) H(72) 111.(2) no
H(71) C(7) H(72) 110.(3) no
C(8) C(9) H(9) 123.(3) no
C(10) C(9) H(9) 129.(3) no
C(9) C(10) H(10) 127.(2) no
C(11) C(10) H(10) 127.(2) no
O(3) C(11) H(11) 113.(2) no
C(10) C(11) H(11) 136.(2) no
C(12) C(13) H(13) 127.5 no
C(14) C(13) H(13) 127.5 no
C(13) C(14) H(14) 125.(3) no
C(15) C(14) H(14) 127.(3) no
O(4) C(15) H(15) 119.(3) no
C(14) C(15) H(15) 131.(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S C(1) . . 1.796(4) yes
S C(4) . . 1.751(3) yes
O(1) N(5) . . 1.240(3) yes
O(2) N(5) . . 1.251(3) yes
O(3) C(8) . . 1.377(3) yes
O(3) C(11) . . 1.371(4) yes
O(4) C(12) . . 1.368(4) yes
O(4) C(15) . . 1.389(5) yes
N(1) C(2) . . 1.336(4) yes
N(1) C(6) . . 1.350(4) yes
N(3) C(2) . . 1.353(4) yes
N(3) C(4) . . 1.325(4) yes
N(5) C(5) . . 1.417(4) yes
N(6) C(6) . . 1.346(4) yes
N(6) C(7) . . 1.469(4) yes
C(2) C(12) . . 1.450(4) yes
C(4) C(5) . . 1.422(4) yes
C(5) C(6) . . 1.428(4) yes
C(7) C(8) . . 1.479(4) yes
C(8) C(9) . . 1.337(4) yes
C(9) C(10) . . 1.424(5) yes
C(10) C(11) . . 1.339(5) yes
C(12) C(13) . . 1.341(4) yes
C(13) C(14) . . 1.426(5) yes
C(14) C(15) . . 1.319(6) yes
N(6) H(6) . . 0.92(3) no
C(1) H(101) . . 0.98(4) no
C(1) H(102) . . 0.94(3) no
C(1) H(103) . . 0.95(3) no
C(7) H(71) . . 0.99(3) no
C(7) H(72) . . 0.95(3) no
C(9) H(9) . . 0.87(4) no
C(10) H(10) . . 0.95(3) no
C(11) H(11) . . 0.98(4) no
C(13) H(13) . . 0.949 no
C(14) H(14) . . 0.89(4) no
C(15) H(15) . . 0.95(4) no
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_publ_flag
S C(4) N(3) C(2) 179.7(2) no
S C(4) C(5) N(5) 1.1(4) no
S C(4) C(5) C(6) -178.0(2) no
O(1) N(5) C(5) C(4) 4.8(4) no
O(1) N(5) C(5) C(6) -176.1(3) no
O(2) N(5) C(5) C(4) -176.8(3) no
O(2) N(5) C(5) C(6) 2.3(4) no
O(3) C(8) C(7) N(6) -70.2(3) no
O(3) C(8) C(9) C(10) -0.9(4) no
O(3) C(11) C(10) C(9) -0.4(4) no
O(4) C(12) C(2) N(1) 0.9(4) no
O(4) C(12) C(2) N(3) -179.4(3) no
O(4) C(12) C(13) C(14) 1.3(4) no
O(4) C(15) C(14) C(13) 1.4(5) no
N(1) C(2) N(3) C(4) -1.1(4) no
N(1) C(2) C(12) C(13) 179.7(3) no
N(1) C(6) N(6) C(7) -3.8(4) no
N(1) C(6) C(5) N(5) 178.5(3) no
N(1) C(6) C(5) C(4) -2.4(4) no
N(3) C(2) N(1) C(6) -0.1(4) no
N(3) C(2) C(12) C(13) -0.6(5) no
N(3) C(4) S C(1) -4.8(3) no
N(3) C(4) C(5) N(5) -179.7(3) no
N(3) C(4) C(5) C(6) 1.2(4) no
N(5) C(5) C(6) N(6) -0.9(5) no
N(6) C(6) N(1) C(2) -178.7(3) no
N(6) C(6) C(5) C(4) 178.2(3) no
N(6) C(7) C(8) C(9) 111.9(4) no
C(1) S C(4) C(5) 174.4(3) no
C(2) N(1) C(6) C(5) 1.9(4) no
C(2) N(3) C(4) C(5) 0.4(4) no
C(2) C(12) O(4) C(15) 178.5(3) no
C(2) C(12) C(13) C(14) -177.6(3) no
C(4) N(3) C(2) C(12) 179.3(3) no
C(5) C(6) N(6) C(7) 175.7(3) no
C(6) N(1) C(2) C(12) 179.5(3) no
C(6) N(6) C(7) C(8) -77.5(4) no
C(7) C(8) O(3) C(11) -177.8(3) no
C(7) C(8) C(9) C(10) 177.2(3) no
C(8) O(3) C(11) C(10) -0.2(4) no
C(8) C(9) C(10) C(11) 0.7(4) no
C(9) C(8) O(3) C(11) 0.6(3) no
C(12) O(4) C(15) C(14) -0.6(5) no
C(12) C(13) C(14) C(15) -1.7(5) no
C(13) C(12) O(4) C(15) -0.5(4) no
