4,5,6-Trimethyl-2-(phenyl­sulfon­ylamino)pyrimidine

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.

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

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Computing details

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

Crystal data

C13H15N3O2S	Z = 2
Mr = 277.34	F(000) = 292
Triclinic, P1	Dx = 1.351 Mg m^−3
a = 7.7014 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.831 (2) Å	Cell parameters from 1324 reflections
c = 10.849 (3) Å	θ = 2.4–25.8°
α = 83.894 (4)°	µ = 0.24 mm^−1
β = 70.965 (4)°	T = 294 K
γ = 78.118 (4)°	Prism, colourless
V = 682.0 (3) Å^3	0.20 × 0.18 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2399 independent reflections
Radiation source: fine-focus sealed tube	1743 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS, Sheldrick, 1996)	h = −4→9
Tmin = 0.954, Tmax = 0.967	k = −10→10
3506 measured reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0691P)^2 + 0.0938P] where P = (Fo^2 + 2Fc^2)/3
2399 reflections	(Δ/σ)max = 0.002
175 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	1.07613 (9)	0.78899 (8)	0.62198 (6)	0.0438 (2)
O1	1.1554 (2)	0.8495 (2)	0.49195 (16)	0.0524 (5)
O2	1.1969 (2)	0.6942 (2)	0.68558 (18)	0.0579 (5)
N1	0.9694 (3)	0.9444 (2)	0.70339 (19)	0.0481 (6)
H1	0.9719	1.0314	0.6595	0.058*
N2	0.8650 (3)	0.8177 (3)	0.9053 (2)	0.0503 (6)
N3	0.8026 (3)	1.0927 (2)	0.8792 (2)	0.0469 (5)
C1	0.9028 (3)	0.6874 (3)	0.6210 (2)	0.0383 (6)
C2	0.7814 (4)	0.7509 (3)	0.5519 (2)	0.0469 (6)
H2	0.7909	0.8460	0.5067	0.056*
C3	0.6460 (4)	0.6710 (3)	0.5510 (3)	0.0558 (7)
H3	0.5624	0.7126	0.5054	0.067*
C4	0.6340 (4)	0.5305 (3)	0.6171 (3)	0.0567 (8)
H4	0.5422	0.4772	0.6160	0.068*
C5	0.7557 (4)	0.4677 (3)	0.6847 (3)	0.0580 (8)
H5	0.7474	0.3718	0.7285	0.070*
C6	0.8914 (4)	0.5473 (3)	0.6876 (3)	0.0515 (7)
H6	0.9737	0.5061	0.7342	0.062*
C7	0.8741 (3)	0.9506 (3)	0.8377 (2)	0.0428 (6)
C8	0.7745 (4)	0.8295 (3)	1.0347 (3)	0.0523 (7)
C9	0.6961 (4)	0.9712 (3)	1.0911 (2)	0.0505 (7)
C10	0.7131 (4)	1.1018 (3)	1.0084 (3)	0.0505 (7)
C11	0.7637 (6)	0.6790 (4)	1.1117 (3)	0.0920 (12)
H11A	0.8223	0.5949	1.0542	0.138*
H11B	0.6351	0.6715	1.1549	0.138*
H11C	0.8268	0.6738	1.1756	0.138*
C12	0.5963 (5)	0.9816 (4)	1.2355 (3)	0.0763 (10)
H12A	0.5454	1.0880	1.2560	0.114*
H12B	0.6828	0.9401	1.2826	0.114*
H12C	0.4970	0.9232	1.2599	0.114*
C13	0.6350 (5)	1.2629 (4)	1.0559 (3)	0.0779 (10)
H13A	0.6552	1.3361	0.9830	0.117*
H13B	0.6964	1.2835	1.1148	0.117*
H13C	0.5034	1.2721	1.1005	0.117*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0397 (4)	0.0513 (4)	0.0389 (4)	−0.0098 (3)	−0.0079 (3)	−0.0062 (3)
O1	0.0484 (11)	0.0624 (12)	0.0404 (10)	−0.0177 (9)	−0.0005 (8)	−0.0036 (9)
O2	0.0466 (11)	0.0728 (13)	0.0567 (12)	−0.0040 (10)	−0.0221 (9)	−0.0072 (10)
N1	0.0613 (14)	0.0438 (12)	0.0365 (12)	−0.0160 (10)	−0.0074 (10)	−0.0032 (10)
N2	0.0606 (14)	0.0485 (13)	0.0400 (12)	−0.0097 (11)	−0.0129 (11)	−0.0029 (10)
N3	0.0565 (14)	0.0459 (13)	0.0408 (12)	−0.0104 (10)	−0.0157 (10)	−0.0086 (10)
C1	0.0382 (13)	0.0396 (13)	0.0330 (13)	−0.0043 (11)	−0.0057 (11)	−0.0070 (11)
C2	0.0460 (15)	0.0464 (15)	0.0469 (15)	−0.0098 (12)	−0.0133 (12)	0.0029 (12)
C3	0.0502 (17)	0.0651 (19)	0.0551 (17)	−0.0126 (14)	−0.0190 (14)	−0.0033 (15)
C4	0.0547 (17)	0.0624 (19)	0.0547 (17)	−0.0238 (14)	−0.0079 (14)	−0.0137 (15)
C5	0.072 (2)	0.0418 (15)	0.0559 (18)	−0.0180 (14)	−0.0094 (16)	−0.0017 (13)
C6	0.0601 (18)	0.0457 (15)	0.0475 (16)	−0.0034 (13)	−0.0191 (13)	−0.0023 (13)
C7	0.0450 (15)	0.0522 (16)	0.0354 (14)	−0.0134 (12)	−0.0144 (11)	−0.0044 (12)
C8	0.0559 (17)	0.0596 (17)	0.0407 (15)	−0.0109 (13)	−0.0152 (13)	0.0014 (13)
C9	0.0477 (16)	0.0680 (18)	0.0370 (14)	−0.0081 (13)	−0.0152 (12)	−0.0061 (14)
C10	0.0497 (16)	0.0597 (17)	0.0475 (16)	−0.0045 (13)	−0.0218 (13)	−0.0148 (14)
C11	0.128 (3)	0.074 (2)	0.058 (2)	−0.017 (2)	−0.014 (2)	0.0120 (18)
C12	0.078 (2)	0.100 (3)	0.0438 (18)	−0.0098 (19)	−0.0103 (16)	−0.0127 (17)
C13	0.099 (3)	0.067 (2)	0.062 (2)	0.0071 (18)	−0.0247 (19)	−0.0247 (17)

Geometric parameters (Å, º)

S1—O2	1.4202 (19)	C5—C6	1.384 (4)
S1—O1	1.4354 (18)	C5—H5	0.9300
S1—N1	1.630 (2)	C6—H6	0.9300
S1—C1	1.758 (2)	C8—C9	1.384 (4)
N1—C7	1.403 (3)	C8—C11	1.496 (4)
N1—H1	0.8600	C9—C10	1.385 (4)
N2—C7	1.318 (3)	C9—C12	1.506 (4)
N2—C8	1.353 (3)	C10—C13	1.501 (4)
N3—C7	1.325 (3)	C11—H11A	0.9600
N3—C10	1.348 (3)	C11—H11B	0.9600
C1—C6	1.369 (4)	C11—H11C	0.9600
C1—C2	1.379 (3)	C12—H12A	0.9600
C2—C3	1.377 (4)	C12—H12B	0.9600
C2—H2	0.9300	C12—H12C	0.9600
C3—C4	1.371 (4)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.368 (4)	C13—H13C	0.9600
C4—H4	0.9300
O2—S1—O1	118.78 (11)	N2—C7—N1	117.2 (2)
O2—S1—N1	110.06 (11)	N3—C7—N1	114.2 (2)
O1—S1—N1	103.20 (11)	N2—C8—C9	122.1 (3)
O2—S1—C1	108.88 (12)	N2—C8—C11	115.3 (3)
O1—S1—C1	108.30 (11)	C9—C8—C11	122.6 (3)
N1—S1—C1	106.96 (11)	C8—C9—C10	116.8 (2)
C7—N1—S1	126.63 (19)	C8—C9—C12	121.2 (3)
C7—N1—H1	116.7	C10—C9—C12	122.0 (3)
S1—N1—H1	116.7	N3—C10—C9	122.1 (2)
C7—N2—C8	115.1 (2)	N3—C10—C13	115.3 (3)
C7—N3—C10	115.3 (2)	C9—C10—C13	122.6 (3)
C6—C1—C2	121.4 (2)	C8—C11—H11A	109.5
C6—C1—S1	119.7 (2)	C8—C11—H11B	109.5
C2—C1—S1	118.91 (19)	H11A—C11—H11B	109.5
C3—C2—C1	118.8 (2)	C8—C11—H11C	109.5
C3—C2—H2	120.6	H11A—C11—H11C	109.5
C1—C2—H2	120.6	H11B—C11—H11C	109.5
C4—C3—C2	120.2 (3)	C9—C12—H12A	109.5
C4—C3—H3	119.9	C9—C12—H12B	109.5
C2—C3—H3	119.9	H12A—C12—H12B	109.5
C5—C4—C3	120.7 (3)	C9—C12—H12C	109.5
C5—C4—H4	119.7	H12A—C12—H12C	109.5
C3—C4—H4	119.7	H12B—C12—H12C	109.5
C4—C5—C6	119.9 (3)	C10—C13—H13A	109.5
C4—C5—H5	120.1	C10—C13—H13B	109.5
C6—C5—H5	120.1	H13A—C13—H13B	109.5
C1—C6—C5	119.1 (3)	C10—C13—H13C	109.5
C1—C6—H6	120.4	H13A—C13—H13C	109.5
C5—C6—H6	120.4	H13B—C13—H13C	109.5
N2—C7—N3	128.6 (2)
O2—S1—N1—C7	−49.7 (2)	C8—N2—C7—N1	178.9 (2)
O1—S1—N1—C7	−177.4 (2)	C10—N3—C7—N2	1.9 (4)
C1—S1—N1—C7	68.5 (2)	C10—N3—C7—N1	−178.9 (2)
O2—S1—C1—C6	6.4 (2)	S1—N1—C7—N2	−1.8 (3)
O1—S1—C1—C6	136.9 (2)	S1—N1—C7—N3	178.85 (17)
N1—S1—C1—C6	−112.5 (2)	C7—N2—C8—C9	0.5 (4)
O2—S1—C1—C2	−173.18 (18)	C7—N2—C8—C11	179.9 (3)
O1—S1—C1—C2	−42.7 (2)	N2—C8—C9—C10	0.5 (4)
N1—S1—C1—C2	67.9 (2)	C11—C8—C9—C10	−178.8 (3)
C6—C1—C2—C3	0.3 (4)	N2—C8—C9—C12	−179.9 (3)
S1—C1—C2—C3	179.86 (19)	C11—C8—C9—C12	0.8 (5)
C1—C2—C3—C4	−0.5 (4)	C7—N3—C10—C9	−0.6 (4)
C2—C3—C4—C5	0.0 (4)	C7—N3—C10—C13	179.0 (2)
C3—C4—C5—C6	0.6 (4)	C8—C9—C10—N3	−0.5 (4)
C2—C1—C6—C5	0.3 (4)	C12—C9—C10—N3	179.9 (2)
S1—C1—C6—C5	−179.20 (19)	C8—C9—C10—C13	180.0 (3)
C4—C5—C6—C1	−0.8 (4)	C12—C9—C10—C13	0.4 (4)
C8—N2—C7—N3	−1.8 (4)