#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/91/2019142.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_2019142
loop_
_publ_author_name
'Trilleras, Jorge'
'Ramos, Juan'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 5,5'-Methylenebis[6-amino-3-methyl-2-methylsulfanylpyrimidin-4(3H)-one]:
 an unusual molecular geometry within a hydrogen-bonded molecular ribbon
;
_journal_coeditor_code           UK3079
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1043
_journal_page_last               1046
_journal_paper_doi               10.1107/S0108270113020465
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C13 H18 N6 O2 S2'
_chemical_formula_moiety         'C13 H18 N6 O2 S2'
_chemical_formula_sum            'C13 H18 N6 O2 S2'
_chemical_formula_weight         354.47
_chemical_name_common
;
Bis(6-amino-3-methyl-2-methylsulfanyl-4-oxopyrimidin-5-yl)methane
;
_chemical_name_systematic
;
5,5'-Methylenebis[6-amino-3-methyl-2-methylsulfanylpyrimidin-4(3H)-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
_cell_angle_alpha                90.00
_cell_angle_beta                 133.61(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.862(6)
_cell_length_b                   7.4877(19)
_cell_length_c                   14.236(5)
_cell_measurement_reflns_used    1763
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.86
_cell_volume                     1533.0(10)
_computing_cell_refinement
'DIRAX/LSQ (Duisenberg et al., 2000)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10706
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.86
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.469
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         1763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0598P)²+1.8314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                1442
_reflns_number_total             1763
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            uk3079.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2019142
_cod_database_fobs_code          2019142
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.40451(10) 0.2749(2) 0.37455(14) 0.0221(3) Uani d . 1 1
C C2 0.47983(12) 0.2819(2) 0.49776(17) 0.0210(4) Uani d . 1 1
N N3 0.56632(10) 0.2293(2) 0.55153(14) 0.0218(3) Uani d . 1 1
C C4 0.57747(13) 0.1544(2) 0.47152(18) 0.0213(4) Uani d . 1 1
C C5 0.49617(13) 0.1386(2) 0.33850(18) 0.0213(4) Uani d . 1 1
C C6 0.41280(13) 0.2054(2) 0.29338(17) 0.0218(4) Uani d . 1 1
S S21 0.47580(3) 0.36659(6) 0.60877(4) 0.02434(17) Uani d . 1 1
C C21 0.35233(14) 0.3784(3) 0.5089(2) 0.0300(4) Uani d . 1 1
H H21A 0.3243 0.4568 0.4346 0.045 Uiso calc R 1 1
H H21B 0.3400 0.4262 0.5599 0.045 Uiso calc R 1 1
H H21C 0.3254 0.2586 0.4777 0.045 Uiso calc R 1 1
C C31 0.64794(13) 0.2467(3) 0.69125(18) 0.0275(4) Uani d . 1 1
H H31A 0.6598 0.3733 0.7152 0.041 Uiso calc R 1 1
H H31B 0.7022 0.1939 0.7124 0.041 Uiso calc R 1 1
H H31C 0.6363 0.1844 0.7394 0.041 Uiso calc R 1 1
O O41 0.65766(9) 0.10876(18) 0.52349(13) 0.0255(3) Uani d . 1 1
C C51 0.5000 0.0381(4) 0.2500 0.0227(5) Uani d S 1 2
H H51A 0.4448 -0.0407 0.1945 0.027 Uiso calc PR 0.50 1
H H51B 0.5552 -0.0407 0.3055 0.027 Uiso calc PR 0.50 1
N N61 0.33348(11) 0.2033(2) 0.16687(15) 0.0274(4) Uani d . 1 1
H H61A 0.3307 0.1749 0.1042 0.033 Uiso d R 1 1
H H61B 0.2844 0.2608 0.1408 0.033 Uiso d R 1 1
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C6 . . 117.02(16) ?
N1 C2 N3 . . 124.99(16) ?
N1 C2 S21 . . 120.24(14) ?
N3 C2 S21 . . 114.76(13) ?
C2 N3 C4 . . 119.68(15) ?
C2 N3 C31 . . 121.27(15) ?
C4 N3 C31 . . 119.04(15) ?
O41 C4 C5 . . 125.50(17) ?
O41 C4 N3 . . 118.18(16) ?
C5 C4 N3 . . 116.32(16) ?
C6 C5 C4 . . 119.04(17) ?
C6 C5 C51 . . 121.42(15) ?
C4 C5 C51 . . 119.40(15) ?
N61 C6 N1 . . 114.86(17) ?
N61 C6 C5 . . 122.35(17) ?
N1 C6 C5 . . 122.77(17) ?
C2 S21 C21 . . 100.96(10) ?
S21 C21 H21A . . 109.5 ?
S21 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
S21 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
N3 C31 H31A . . 109.5 ?
N3 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
N3 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
C5 C51 C5 . 2_655 120.3(2) y
C5 C51 H51A . . 107.2 ?
C5 C51 H51A 2_655 . 107.2 ?
C5 C51 H51B . . 107.2 ?
C5 C51 H51B 2_655 . 107.2 ?
H51A C51 H51B . . 106.9 ?
C6 N61 H61A . . 123.8 ?
C6 N61 H61B . . 119.5 ?
H61A N61 H61B . . 114.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.303(2) ?
N1 C6 . 1.377(2) ?
C2 N3 . 1.370(2) ?
C2 S21 . 1.7553(19) ?
N3 C4 . 1.417(2) ?
N3 C31 . 1.467(2) ?
C4 O41 . 1.255(2) ?
C4 C5 . 1.410(3) ?
C5 C6 . 1.392(3) ?
C5 C51 . 1.514(2) y
C6 N61 . 1.346(2) ?
S21 C21 . 1.798(2) ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C31 H31A . 0.9800 ?
C31 H31B . 0.9800 ?
C31 H31C . 0.9800 ?
C51 C5 2_655 1.514(2) ?
C51 H51A . 0.9900 ?
C51 H51B . 0.9900 ?
N61 H61A . 0.8798 ?
N61 H61B . 0.8800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N61 H61A O41 2_655 0.88 2.05 2.921(3) 173 y
N61 H61B O41 8_455 0.88 2.07 2.917(3) 162 y
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_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 N3 . 1.6(3) ?
C6 N1 C2 S21 . -179.46(13) ?
N1 C2 N3 C4 . -2.6(3) ?
S21 C2 N3 C4 . 178.35(13) ?
N1 C2 N3 C31 . 178.27(18) ?
S21 C2 N3 C31 . -0.8(2) ?
C2 N3 C4 O41 . 179.51(16) ?
C31 N3 C4 O41 . -1.4(3) ?
C2 N3 C4 C5 . -0.2(2) ?
C31 N3 C4 C5 . 178.98(16) ?
O41 C4 C5 C6 . -175.99(17) ?
N3 C4 C5 C6 . 3.6(2) ?
O41 C4 C5 C51 . 8.4(3) ?
N3 C4 C5 C51 . -171.97(16) ?
C2 N1 C6 N61 . -179.08(17) ?
C2 N1 C6 C5 . 2.3(3) ?
C4 C5 C6 N61 . 176.56(18) ?
C51 C5 C6 N61 . -7.9(3) ?
C4 C5 C6 N1 . -4.9(3) ?
C51 C5 C6 N1 . 170.59(18) ?
N1 C2 S21 C21 . 11.36(18) y
N3 C2 S21 C21 . -169.56(14) y
C4 C5 C51 C5 2_655 -102.25(17) y
C6 C5 C51 C5 2_655 82.24(17) y
