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The title compound, C11H10N4OS2, has a twofold axis passing through the carbonyl group. The mol­ecules stack along the b axis via π–π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003715/ob6475sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003715/ob6475Isup2.hkl
Contains datablock I

CCDC reference: 269836

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.062
  • wR factor = 0.106
  • Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.775 0.975 Tmin' and Tmax expected: 0.950 0.975 RR' = 0.816 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.81 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART and SAINT (Siemens, 1994); data reduction: SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXL97.

1,3-Bis(pyrimidin-2-ylsulfanyl)propan-2-one top
Crystal data top
C11H10N4OS2Dx = 1.489 Mg m3
Mr = 278.35Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcnCell parameters from 6883 reflections
a = 7.8042 (11) Åθ = 1.9–25.0°
b = 7.3159 (11) ŵ = 0.42 mm1
c = 21.753 (3) ÅT = 293 K
V = 1242.0 (3) Å3Needle, yellow
Z = 40.12 × 0.10 × 0.06 mm
F(000) = 576
Data collection top
Siemens SMART CCD
diffractometer
1101 independent reflections
Radiation source: fine-focus sealed tube813 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.775, Tmax = 0.975k = 88
6883 measured reflectionsl = 2521
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106All H-atom parameters refined
S = 1.15 w = 1/[σ2(Fo2) + (0.0245P)2 + 1.036P]
where P = (Fo2 + 2Fc2)/3
1101 reflections(Δ/σ)max < 0.001
103 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.61270 (11)0.06990 (17)0.62833 (4)0.0581 (4)
O10.50000.2439 (6)0.75000.0580 (10)
N10.2786 (4)0.0234 (4)0.64747 (12)0.0444 (8)
N20.3689 (4)0.1535 (4)0.55178 (13)0.0495 (8)
C10.2046 (5)0.1674 (6)0.53596 (19)0.0561 (11)
C20.0727 (5)0.1137 (6)0.5730 (2)0.0546 (11)
C30.1163 (5)0.0407 (5)0.62870 (18)0.0483 (9)
C40.3951 (4)0.0820 (5)0.60760 (15)0.0407 (8)
C50.5935 (5)0.0354 (6)0.70243 (18)0.0519 (10)
C60.50000.0782 (8)0.75000.0462 (13)
H1A0.185 (4)0.223 (5)0.4990 (16)0.053 (11)*
H2A0.044 (5)0.125 (5)0.5596 (16)0.065 (12)*
H3A0.030 (4)0.003 (5)0.6596 (16)0.056 (11)*
H5A0.709 (5)0.053 (5)0.7175 (15)0.070 (12)*
H5B0.537 (5)0.153 (6)0.6983 (18)0.076 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0412 (5)0.0825 (8)0.0505 (6)0.0012 (6)0.0024 (5)0.0035 (6)
O10.073 (3)0.050 (3)0.050 (2)0.0000.006 (2)0.000
N10.0428 (16)0.0467 (19)0.0439 (17)0.0015 (15)0.0021 (15)0.0011 (14)
N20.0540 (18)0.056 (2)0.0389 (17)0.0019 (16)0.0007 (16)0.0041 (15)
C10.068 (3)0.054 (3)0.046 (2)0.002 (2)0.015 (2)0.004 (2)
C20.044 (2)0.053 (3)0.066 (3)0.001 (2)0.014 (2)0.006 (2)
C30.044 (2)0.048 (2)0.053 (2)0.003 (2)0.001 (2)0.004 (2)
C40.0419 (19)0.041 (2)0.0388 (19)0.0020 (19)0.0004 (17)0.0047 (17)
C50.045 (2)0.061 (3)0.049 (2)0.012 (2)0.004 (2)0.002 (2)
C60.040 (3)0.055 (4)0.043 (3)0.0000.011 (2)0.000
Geometric parameters (Å, º) top
S1—C41.759 (3)C1—H1A0.91 (3)
S1—C51.793 (4)C2—C31.368 (5)
O1—C61.212 (6)C2—H2A0.96 (4)
N1—C41.327 (4)C3—H3A1.00 (4)
N1—C31.336 (4)C5—C61.515 (5)
N2—C11.332 (5)C5—H5A0.96 (4)
N2—C41.338 (4)C5—H5B0.97 (4)
C1—C21.364 (5)C6—C5i1.515 (5)
C4—S1—C599.86 (18)N1—C4—N2127.9 (3)
C4—N1—C3114.8 (3)N1—C4—S1118.5 (3)
C1—N2—C4114.3 (3)N2—C4—S1113.6 (3)
N2—C1—C2123.5 (4)C6—C5—S1114.8 (3)
N2—C1—H1A115 (2)C6—C5—H5A107 (2)
C2—C1—H1A122 (2)S1—C5—H5A107 (2)
C1—C2—C3116.6 (4)C6—C5—H5B109 (2)
C1—C2—H2A121 (2)S1—C5—H5B110 (2)
C3—C2—H2A123 (2)H5A—C5—H5B110 (3)
N1—C3—C2122.9 (4)O1—C6—C5123.3 (3)
N1—C3—H3A114 (2)O1—C6—C5i123.3 (3)
C2—C3—H3A124 (2)C5—C6—C5i113.4 (5)
C4—N2—C1—C20.1 (6)C1—N2—C4—S1178.6 (3)
N2—C1—C2—C30.7 (6)C5—S1—C4—N12.1 (3)
C4—N1—C3—C20.3 (5)C5—S1—C4—N2178.6 (3)
C1—C2—C3—N10.9 (6)C4—S1—C5—C664.2 (3)
C3—N1—C4—N20.5 (5)S1—C5—C6—O129.7 (3)
C3—N1—C4—S1178.7 (3)S1—C5—C6—C5i150.3 (3)
C1—N2—C4—N10.7 (6)
Symmetry code: (i) x+1, y, z+3/2.
 

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