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In the title compound, C12H12N2OS, the dihedral angle between the benzene and pyrimidine rings is 84.1 (1)°. The mol­ecules are linked by centrosymmetric pairs of N—H...O [N...O = 2.817 (2) Å] and N—H...S [N...S = 3.357 (2) Å] hydrogen bonds to form chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805020921/wk6057sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805020921/wk6057Isup2.hkl
Contains datablock I

CCDC reference: 276172

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.123
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.67 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C11
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Brker, 2001); software used to prepare material for publication: SHELXTL.

5-benzyl-6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one top
Crystal data top
C12H12N2OSF(000) = 488
Mr = 232.30Dx = 1.332 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ynCell parameters from 1539 reflections
a = 5.8779 (9) Åθ = 2.7–23.4°
b = 29.800 (4) ŵ = 0.26 mm1
c = 7.2160 (11) ÅT = 292 K
β = 113.622 (2)°Block, colorless
V = 1158.1 (3) Å30.20 × 0.08 × 0.06 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2274 independent reflections
Radiation source: fine-focus sealed tube1753 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
0.3° ω scansθmax = 26.1°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 74
Tmin = 0.950, Tmax = 0.985k = 3236
5152 measured reflectionsl = 88
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.058P)2 + 0.2016P]
where P = (Fo2 + 2Fc2)/3
2274 reflections(Δ/σ)max < 0.001
146 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.16 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
C20.5675 (4)0.00697 (7)0.7906 (3)0.0412 (5)
C40.2035 (4)0.05504 (7)0.6485 (3)0.0458 (5)
C50.3509 (4)0.09261 (7)0.7549 (3)0.0436 (5)
C60.5918 (4)0.08551 (7)0.8763 (3)0.0449 (5)
C70.7674 (5)0.11984 (8)1.0091 (4)0.0670 (7)
H7A0.70630.14930.96130.100*
H7B0.92790.11591.00590.100*
H7C0.78070.11631.14530.100*
C80.2217 (4)0.13688 (8)0.7296 (3)0.0540 (6)
H8A0.30690.15450.85090.065*
H8B0.05440.13150.71950.065*
C90.2055 (4)0.16450 (7)0.5496 (3)0.0486 (6)
C100.0270 (5)0.19793 (9)0.4811 (5)0.0763 (8)
H100.08100.20230.54480.092*
C110.0078 (8)0.22450 (11)0.3210 (6)0.1104 (14)
H110.11380.24660.27670.132*
C120.1634 (9)0.21904 (13)0.2262 (6)0.1088 (14)
H120.14950.23740.11810.131*
C130.3407 (7)0.18634 (12)0.2904 (4)0.0866 (10)
H130.44800.18250.22570.104*
C140.3618 (5)0.15881 (9)0.4521 (3)0.0599 (7)
H140.48220.13640.49430.072*
N10.6932 (3)0.04336 (6)0.8898 (3)0.0456 (4)
H10.84770.04010.96720.055*
N30.3240 (3)0.01424 (6)0.6757 (2)0.0449 (4)
H30.23660.00860.61430.054*
O10.0202 (3)0.05739 (6)0.5398 (3)0.0626 (5)
S10.69904 (11)0.043343 (19)0.80797 (9)0.0515 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0386 (11)0.0476 (13)0.0346 (10)0.0022 (10)0.0117 (9)0.0043 (9)
C40.0417 (12)0.0481 (14)0.0436 (11)0.0034 (10)0.0128 (10)0.0038 (10)
C50.0449 (13)0.0430 (13)0.0417 (11)0.0005 (10)0.0160 (10)0.0030 (9)
C60.0472 (13)0.0423 (13)0.0447 (11)0.0024 (10)0.0180 (11)0.0004 (9)
C70.0553 (15)0.0546 (16)0.0797 (17)0.0091 (12)0.0151 (14)0.0149 (13)
C80.0512 (14)0.0523 (14)0.0568 (14)0.0047 (11)0.0197 (12)0.0069 (11)
C90.0436 (13)0.0365 (12)0.0503 (12)0.0054 (10)0.0027 (10)0.0057 (10)
C100.0615 (17)0.0496 (16)0.094 (2)0.0118 (14)0.0057 (15)0.0007 (15)
C110.097 (3)0.057 (2)0.125 (3)0.009 (2)0.009 (2)0.029 (2)
C120.111 (3)0.082 (3)0.085 (2)0.037 (2)0.010 (2)0.035 (2)
C130.087 (2)0.096 (2)0.0639 (17)0.030 (2)0.0163 (16)0.0091 (17)
C140.0572 (15)0.0581 (16)0.0540 (14)0.0035 (13)0.0115 (12)0.0034 (12)
N10.0333 (9)0.0473 (11)0.0472 (10)0.0002 (8)0.0068 (8)0.0005 (8)
N30.0394 (10)0.0413 (10)0.0436 (9)0.0018 (8)0.0059 (8)0.0002 (8)
O10.0416 (9)0.0563 (11)0.0700 (11)0.0058 (8)0.0016 (8)0.0024 (8)
S10.0452 (4)0.0462 (4)0.0546 (4)0.0043 (3)0.0111 (3)0.0014 (3)
Geometric parameters (Å, º) top
C2—N11.346 (3)C8—H8B0.9700
C2—N31.354 (3)C9—C141.373 (3)
C2—S11.668 (2)C9—C101.386 (3)
C4—O11.234 (3)C10—C111.367 (5)
C4—N31.381 (3)C10—H100.9300
C4—C51.435 (3)C11—C121.353 (5)
C5—C61.350 (3)C11—H110.9300
C5—C81.497 (3)C12—C131.365 (5)
C6—N11.377 (3)C12—H120.9300
C6—C71.496 (3)C13—C141.391 (4)
C7—H7A0.9600C13—H130.9300
C7—H7B0.9600C14—H140.9300
C7—H7C0.9600N1—H10.8600
C8—C91.508 (3)N3—H30.8600
C8—H8A0.9700
N1—C2—N3114.66 (19)C14—C9—C10118.2 (2)
N1—C2—S1123.03 (16)C14—C9—C8123.3 (2)
N3—C2—S1122.31 (16)C10—C9—C8118.5 (2)
O1—C4—N3119.7 (2)C11—C10—C9120.8 (3)
O1—C4—C5123.8 (2)C11—C10—H10119.6
N3—C4—C5116.45 (19)C9—C10—H10119.6
C6—C5—C4118.4 (2)C12—C11—C10120.9 (3)
C6—C5—C8124.5 (2)C12—C11—H11119.5
C4—C5—C8117.02 (19)C10—C11—H11119.5
C5—C6—N1120.04 (19)C11—C12—C13119.5 (3)
C5—C6—C7125.7 (2)C11—C12—H12120.2
N1—C6—C7114.24 (19)C13—C12—H12120.2
C6—C7—H7A109.5C12—C13—C14120.3 (3)
C6—C7—H7B109.5C12—C13—H13119.8
H7A—C7—H7B109.5C14—C13—H13119.8
C6—C7—H7C109.5C9—C14—C13120.3 (3)
H7A—C7—H7C109.5C9—C14—H14119.9
H7B—C7—H7C109.5C13—C14—H14119.9
C5—C8—C9116.11 (19)C2—N1—C6124.58 (19)
C5—C8—H8A108.3C2—N1—H1117.7
C9—C8—H8A108.3C6—N1—H1117.7
C5—C8—H8B108.3C2—N3—C4125.75 (19)
C9—C8—H8B108.3C2—N3—H3117.1
H8A—C8—H8B107.4C4—N3—H3117.1
O1—C4—C5—C6177.2 (2)C9—C10—C11—C120.4 (5)
N3—C4—C5—C61.6 (3)C10—C11—C12—C130.5 (6)
O1—C4—C5—C80.2 (3)C11—C12—C13—C140.0 (5)
N3—C4—C5—C8178.99 (18)C10—C9—C14—C130.6 (3)
C4—C5—C6—N12.5 (3)C8—C9—C14—C13178.2 (2)
C8—C5—C6—N1179.68 (19)C12—C13—C14—C90.5 (4)
C4—C5—C6—C7175.4 (2)N3—C2—N1—C61.6 (3)
C8—C5—C6—C71.8 (3)S1—C2—N1—C6178.81 (16)
C6—C5—C8—C996.4 (3)C5—C6—N1—C20.8 (3)
C4—C5—C8—C986.3 (3)C7—C6—N1—C2177.3 (2)
C5—C8—C9—C1421.2 (3)N1—C2—N3—C42.6 (3)
C5—C8—C9—C10160.0 (2)S1—C2—N3—C4177.84 (16)
C14—C9—C10—C110.1 (4)O1—C4—N3—C2179.91 (19)
C8—C9—C10—C11178.7 (3)C5—C4—N3—C21.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O1i0.861.962.817 (2)176
N1—H1···S1ii0.862.513.3574 (19)171
Symmetry codes: (i) x, y, z+1; (ii) x+2, y, z+2.
 

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