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In the crystal structure of the title compound, C13H15N3O2S, there are inter­molecular N—H...O hydrogen-bond inter­actions and they give rise to dimers of the title compound. In the title mol­ecule, the plane of the pyrimidine ring makes an angle of 81.90 (8)° with the plane of the benzene ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033472/sg2049sup1.cif
Contains datablocks 060607c, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033472/sg2049Isup2.hkl
Contains datablock I

CCDC reference: 621463

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.130
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

4,5,6-trimethyl-2-((phenylsulfonyl)amino)pyrimidine top
Crystal data top
C13H15N3O2SZ = 2
Mr = 277.34F(000) = 292
Triclinic, P1Dx = 1.351 Mg m3
a = 7.7014 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.831 (2) ÅCell parameters from 1324 reflections
c = 10.849 (3) Åθ = 2.4–25.8°
α = 83.894 (4)°µ = 0.24 mm1
β = 70.965 (4)°T = 294 K
γ = 78.118 (4)°Prism, colourless
V = 682.0 (3) Å30.20 × 0.18 × 0.14 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2399 independent reflections
Radiation source: fine-focus sealed tube1743 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS, Sheldrick, 1996)
h = 49
Tmin = 0.954, Tmax = 0.967k = 1010
3506 measured reflectionsl = 1212
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0691P)2 + 0.0938P]
where P = (Fo2 + 2Fc2)/3
2399 reflections(Δ/σ)max = 0.002
175 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.27 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
S11.07613 (9)0.78899 (8)0.62198 (6)0.0438 (2)
O11.1554 (2)0.8495 (2)0.49195 (16)0.0524 (5)
O21.1969 (2)0.6942 (2)0.68558 (18)0.0579 (5)
N10.9694 (3)0.9444 (2)0.70339 (19)0.0481 (6)
H10.97191.03140.65950.058*
N20.8650 (3)0.8177 (3)0.9053 (2)0.0503 (6)
N30.8026 (3)1.0927 (2)0.8792 (2)0.0469 (5)
C10.9028 (3)0.6874 (3)0.6210 (2)0.0383 (6)
C20.7814 (4)0.7509 (3)0.5519 (2)0.0469 (6)
H20.79090.84600.50670.056*
C30.6460 (4)0.6710 (3)0.5510 (3)0.0558 (7)
H30.56240.71260.50540.067*
C40.6340 (4)0.5305 (3)0.6171 (3)0.0567 (8)
H40.54220.47720.61600.068*
C50.7557 (4)0.4677 (3)0.6847 (3)0.0580 (8)
H50.74740.37180.72850.070*
C60.8914 (4)0.5473 (3)0.6876 (3)0.0515 (7)
H60.97370.50610.73420.062*
C70.8741 (3)0.9506 (3)0.8377 (2)0.0428 (6)
C80.7745 (4)0.8295 (3)1.0347 (3)0.0523 (7)
C90.6961 (4)0.9712 (3)1.0911 (2)0.0505 (7)
C100.7131 (4)1.1018 (3)1.0084 (3)0.0505 (7)
C110.7637 (6)0.6790 (4)1.1117 (3)0.0920 (12)
H11A0.82230.59491.05420.138*
H11B0.63510.67151.15490.138*
H11C0.82680.67381.17560.138*
C120.5963 (5)0.9816 (4)1.2355 (3)0.0763 (10)
H12A0.54541.08801.25600.114*
H12B0.68280.94011.28260.114*
H12C0.49700.92321.25990.114*
C130.6350 (5)1.2629 (4)1.0559 (3)0.0779 (10)
H13A0.65521.33610.98300.117*
H13B0.69641.28351.11480.117*
H13C0.50341.27211.10050.117*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0397 (4)0.0513 (4)0.0389 (4)0.0098 (3)0.0079 (3)0.0062 (3)
O10.0484 (11)0.0624 (12)0.0404 (10)0.0177 (9)0.0005 (8)0.0036 (9)
O20.0466 (11)0.0728 (13)0.0567 (12)0.0040 (10)0.0221 (9)0.0072 (10)
N10.0613 (14)0.0438 (12)0.0365 (12)0.0160 (10)0.0074 (10)0.0032 (10)
N20.0606 (14)0.0485 (13)0.0400 (12)0.0097 (11)0.0129 (11)0.0029 (10)
N30.0565 (14)0.0459 (13)0.0408 (12)0.0104 (10)0.0157 (10)0.0086 (10)
C10.0382 (13)0.0396 (13)0.0330 (13)0.0043 (11)0.0057 (11)0.0070 (11)
C20.0460 (15)0.0464 (15)0.0469 (15)0.0098 (12)0.0133 (12)0.0029 (12)
C30.0502 (17)0.0651 (19)0.0551 (17)0.0126 (14)0.0190 (14)0.0033 (15)
C40.0547 (17)0.0624 (19)0.0547 (17)0.0238 (14)0.0079 (14)0.0137 (15)
C50.072 (2)0.0418 (15)0.0559 (18)0.0180 (14)0.0094 (16)0.0017 (13)
C60.0601 (18)0.0457 (15)0.0475 (16)0.0034 (13)0.0191 (13)0.0023 (13)
C70.0450 (15)0.0522 (16)0.0354 (14)0.0134 (12)0.0144 (11)0.0044 (12)
C80.0559 (17)0.0596 (17)0.0407 (15)0.0109 (13)0.0152 (13)0.0014 (13)
C90.0477 (16)0.0680 (18)0.0370 (14)0.0081 (13)0.0152 (12)0.0061 (14)
C100.0497 (16)0.0597 (17)0.0475 (16)0.0045 (13)0.0218 (13)0.0148 (14)
C110.128 (3)0.074 (2)0.058 (2)0.017 (2)0.014 (2)0.0120 (18)
C120.078 (2)0.100 (3)0.0438 (18)0.0098 (19)0.0103 (16)0.0127 (17)
C130.099 (3)0.067 (2)0.062 (2)0.0071 (18)0.0247 (19)0.0247 (17)
Geometric parameters (Å, º) top
S1—O21.4202 (19)C5—C61.384 (4)
S1—O11.4354 (18)C5—H50.9300
S1—N11.630 (2)C6—H60.9300
S1—C11.758 (2)C8—C91.384 (4)
N1—C71.403 (3)C8—C111.496 (4)
N1—H10.8600C9—C101.385 (4)
N2—C71.318 (3)C9—C121.506 (4)
N2—C81.353 (3)C10—C131.501 (4)
N3—C71.325 (3)C11—H11A0.9600
N3—C101.348 (3)C11—H11B0.9600
C1—C61.369 (4)C11—H11C0.9600
C1—C21.379 (3)C12—H12A0.9600
C2—C31.377 (4)C12—H12B0.9600
C2—H20.9300C12—H12C0.9600
C3—C41.371 (4)C13—H13A0.9600
C3—H30.9300C13—H13B0.9600
C4—C51.368 (4)C13—H13C0.9600
C4—H40.9300
O2—S1—O1118.78 (11)N2—C7—N1117.2 (2)
O2—S1—N1110.06 (11)N3—C7—N1114.2 (2)
O1—S1—N1103.20 (11)N2—C8—C9122.1 (3)
O2—S1—C1108.88 (12)N2—C8—C11115.3 (3)
O1—S1—C1108.30 (11)C9—C8—C11122.6 (3)
N1—S1—C1106.96 (11)C8—C9—C10116.8 (2)
C7—N1—S1126.63 (19)C8—C9—C12121.2 (3)
C7—N1—H1116.7C10—C9—C12122.0 (3)
S1—N1—H1116.7N3—C10—C9122.1 (2)
C7—N2—C8115.1 (2)N3—C10—C13115.3 (3)
C7—N3—C10115.3 (2)C9—C10—C13122.6 (3)
C6—C1—C2121.4 (2)C8—C11—H11A109.5
C6—C1—S1119.7 (2)C8—C11—H11B109.5
C2—C1—S1118.91 (19)H11A—C11—H11B109.5
C3—C2—C1118.8 (2)C8—C11—H11C109.5
C3—C2—H2120.6H11A—C11—H11C109.5
C1—C2—H2120.6H11B—C11—H11C109.5
C4—C3—C2120.2 (3)C9—C12—H12A109.5
C4—C3—H3119.9C9—C12—H12B109.5
C2—C3—H3119.9H12A—C12—H12B109.5
C5—C4—C3120.7 (3)C9—C12—H12C109.5
C5—C4—H4119.7H12A—C12—H12C109.5
C3—C4—H4119.7H12B—C12—H12C109.5
C4—C5—C6119.9 (3)C10—C13—H13A109.5
C4—C5—H5120.1C10—C13—H13B109.5
C6—C5—H5120.1H13A—C13—H13B109.5
C1—C6—C5119.1 (3)C10—C13—H13C109.5
C1—C6—H6120.4H13A—C13—H13C109.5
C5—C6—H6120.4H13B—C13—H13C109.5
N2—C7—N3128.6 (2)
O2—S1—N1—C749.7 (2)C8—N2—C7—N1178.9 (2)
O1—S1—N1—C7177.4 (2)C10—N3—C7—N21.9 (4)
C1—S1—N1—C768.5 (2)C10—N3—C7—N1178.9 (2)
O2—S1—C1—C66.4 (2)S1—N1—C7—N21.8 (3)
O1—S1—C1—C6136.9 (2)S1—N1—C7—N3178.85 (17)
N1—S1—C1—C6112.5 (2)C7—N2—C8—C90.5 (4)
O2—S1—C1—C2173.18 (18)C7—N2—C8—C11179.9 (3)
O1—S1—C1—C242.7 (2)N2—C8—C9—C100.5 (4)
N1—S1—C1—C267.9 (2)C11—C8—C9—C10178.8 (3)
C6—C1—C2—C30.3 (4)N2—C8—C9—C12179.9 (3)
S1—C1—C2—C3179.86 (19)C11—C8—C9—C120.8 (5)
C1—C2—C3—C40.5 (4)C7—N3—C10—C90.6 (4)
C2—C3—C4—C50.0 (4)C7—N3—C10—C13179.0 (2)
C3—C4—C5—C60.6 (4)C8—C9—C10—N30.5 (4)
C2—C1—C6—C50.3 (4)C12—C9—C10—N3179.9 (2)
S1—C1—C6—C5179.20 (19)C8—C9—C10—C13180.0 (3)
C4—C5—C6—C10.8 (4)C12—C9—C10—C130.4 (4)
C8—N2—C7—N31.8 (4)
 

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