N-(4,6-Dimethyl-pyrimidin-2-yl)-4-(oxolan-2-ylamino)benzene-sulfonamide.

The title compound, C(16)H(20)N(4)O(3)S, adopts an l-shaped conformation, as seen by the dihedral angle of 76.93 (7)° formed between the two aromatic rings. The most notable feature of the crystal packing is the formation of N-H⋯O and N-H⋯N hydrogen bonds that lead to supra-molecular chains orientated along the b axis.

Related literature

For background to the co-crystallization of active pharmaceutical agents, see: Shan & Zaworotko (2008 ▶). For background to sulfa drugs, see: Caira (2007 ▶); Nishimori et al. (2009 ▶). For the synthesis, see: Fructos et al. (2006 ▶); Kemnitz et al. (1998 ▶). For related studies on co-crystal formation, see: Broker & Tiekink (2008 ▶); Broker et al. (2008 ▶).

Experimental

Crystal data

C16H20N4O3S

M = 348.42

Monoclinic,

a = 10.291 (5) Å

b = 9.592 (4) Å

c = 17.196 (8) Å

β = 106.445 (10)°

V = 1628.0 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 98 K

0.35 × 0.21 × 0.11 mm

Data collection

Rigaku Saturn724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.761, T max = 1.000

11164 measured reflections

3749 independent reflections

3341 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.137

S = 1.10

3749 reflections

225 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043347/hb5159sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043347/hb5159Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H20N4O3S	F(000) = 736
Mr = 348.42	Dx = 1.422 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6601 reflections
a = 10.291 (5) Å	θ = 2.5–40.2°
b = 9.592 (4) Å	µ = 0.22 mm−1
c = 17.196 (8) Å	T = 98 K
β = 106.445 (10)°	Block, colourless
V = 1628.0 (13) Å3	0.35 × 0.21 × 0.11 mm
Z = 4

Saturn724 diffractometer	3749 independent reflections
Radiation source: sealed tube	3341 reflections with I > 2σ(I)
graphite	Rint = 0.046
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 2.1°
ω scans	h = −12→13
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→11
Tmin = 0.761, Tmax = 1.000	l = −22→17
11164 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0464P)2 + 1.4631P] where P = (Fo2 + 2Fc2)/3
3749 reflections	(Δ/σ)max < 0.001
225 parameters	Δρmax = 0.60 e Å−3
2 restraints	Δρmin = −0.39 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
S1	0.31473 (6)	0.75837 (6)	0.11287 (3)	0.02795 (16)
O1	0.23391 (18)	0.71472 (18)	0.03422 (9)	0.0357 (4)
O2	0.45898 (17)	0.76422 (18)	0.12920 (9)	0.0339 (4)
O3	0.03413 (17)	1.4900 (2)	0.10040 (10)	0.0406 (4)
N1	0.40297 (19)	0.74868 (19)	0.29276 (10)	0.0271 (4)
N2	0.27644 (18)	0.53811 (19)	0.29370 (10)	0.0265 (4)
N3	0.2755 (2)	0.6434 (2)	0.17341 (10)	0.0283 (4)
H3N	0.2048	0.5906	0.1512	0.034*
N4	0.1102 (2)	1.3038 (2)	0.18799 (14)	0.0421 (5)
H4N	0.1658	1.3594	0.2227	0.051*
C1	0.3215 (2)	0.6443 (2)	0.25786 (12)	0.0258 (4)
C2	0.4447 (2)	0.7458 (2)	0.37479 (12)	0.0283 (5)
C3	0.4038 (2)	0.6408 (2)	0.41786 (12)	0.0298 (5)
H3	0.4336	0.6395	0.4754	0.036*
C4	0.3183 (2)	0.5378 (2)	0.37529 (12)	0.0283 (4)
C5	0.5376 (3)	0.8614 (3)	0.41506 (14)	0.0378 (5)
H5A	0.6280	0.8455	0.4085	0.057*
H5B	0.5435	0.8637	0.4729	0.057*
H5C	0.5021	0.9506	0.3901	0.057*
C6	0.2706 (3)	0.4199 (3)	0.41651 (14)	0.0348 (5)
H6A	0.1741	0.4032	0.3904	0.052*
H6B	0.2840	0.4432	0.4737	0.052*
H6C	0.3223	0.3357	0.4125	0.052*
C7	0.2564 (2)	0.9212 (2)	0.13414 (12)	0.0279 (4)
C8	0.3417 (2)	1.0138 (2)	0.18760 (13)	0.0291 (5)
H8	0.4334	0.9891	0.2129	0.035*
C9	0.2929 (2)	1.1411 (2)	0.20371 (13)	0.0307 (5)
H9	0.3513	1.2038	0.2402	0.037*
C10	0.1574 (2)	1.1793 (2)	0.16669 (13)	0.0318 (5)
C11	0.0733 (2)	1.0854 (2)	0.11240 (14)	0.0344 (5)
H11	−0.0181	1.1100	0.0862	0.041*
C12	0.1224 (2)	0.9580 (2)	0.09687 (13)	0.0322 (5)
H12	0.0645	0.8949	0.0605	0.039*
C13	−0.0074 (3)	1.3735 (3)	0.14064 (16)	0.0384 (6)
H13	−0.0624	1.3077	0.0991	0.046*
C14	−0.0727 (3)	1.5920 (3)	0.0855 (2)	0.0582 (8)
H14A	−0.1141	1.6035	0.0265	0.070*
H14B	−0.0360	1.6832	0.1085	0.070*
C15	−0.1763 (3)	1.5425 (4)	0.1246 (2)	0.0573 (8)
H15A	−0.2534	1.4971	0.0848	0.069*
H15B	−0.2105	1.6199	0.1513	0.069*
C16	−0.0957 (3)	1.4381 (4)	0.1863 (2)	0.0618 (9)
H16A	−0.0415	1.4851	0.2362	0.074*
H16B	−0.1557	1.3681	0.2007	0.074*

	U11	U22	U33	U12	U13	U23
S1	0.0279 (3)	0.0329 (3)	0.0212 (2)	0.0002 (2)	0.0038 (2)	0.00097 (19)
O1	0.0393 (9)	0.0426 (10)	0.0218 (7)	−0.0014 (8)	0.0032 (7)	−0.0022 (6)
O2	0.0289 (8)	0.0431 (9)	0.0297 (8)	0.0015 (7)	0.0085 (7)	0.0009 (7)
O3	0.0274 (8)	0.0554 (11)	0.0384 (9)	0.0039 (8)	0.0083 (7)	0.0090 (8)
N1	0.0287 (9)	0.0260 (9)	0.0242 (8)	0.0000 (7)	0.0037 (7)	−0.0023 (7)
N2	0.0261 (9)	0.0278 (9)	0.0245 (8)	0.0005 (7)	0.0053 (7)	0.0001 (7)
N3	0.0307 (10)	0.0284 (9)	0.0221 (8)	−0.0028 (8)	0.0013 (7)	−0.0012 (7)
N4	0.0332 (11)	0.0337 (11)	0.0476 (12)	0.0010 (9)	−0.0079 (9)	−0.0087 (9)
C1	0.0250 (10)	0.0260 (10)	0.0246 (9)	0.0039 (8)	0.0042 (8)	−0.0011 (8)
C2	0.0297 (11)	0.0273 (10)	0.0251 (10)	0.0030 (9)	0.0031 (8)	−0.0039 (8)
C3	0.0329 (11)	0.0349 (12)	0.0198 (9)	0.0012 (9)	0.0044 (8)	−0.0017 (8)
C4	0.0277 (11)	0.0310 (11)	0.0265 (10)	0.0024 (9)	0.0080 (8)	0.0005 (8)
C5	0.0430 (14)	0.0333 (12)	0.0319 (11)	−0.0059 (11)	0.0020 (10)	−0.0070 (9)
C6	0.0336 (12)	0.0388 (13)	0.0311 (11)	−0.0018 (10)	0.0075 (10)	0.0042 (9)
C7	0.0262 (11)	0.0297 (11)	0.0253 (10)	−0.0007 (9)	0.0032 (8)	0.0046 (8)
C8	0.0238 (10)	0.0311 (11)	0.0286 (10)	−0.0031 (9)	0.0015 (8)	0.0048 (8)
C9	0.0264 (11)	0.0318 (11)	0.0290 (10)	−0.0064 (9)	−0.0001 (9)	0.0012 (8)
C10	0.0286 (11)	0.0305 (11)	0.0309 (11)	−0.0021 (9)	−0.0001 (9)	0.0012 (9)
C11	0.0268 (11)	0.0338 (12)	0.0355 (11)	−0.0005 (9)	−0.0025 (9)	0.0001 (9)
C12	0.0291 (11)	0.0341 (12)	0.0279 (10)	−0.0030 (9)	−0.0011 (9)	0.0000 (9)
C13	0.0300 (12)	0.0293 (12)	0.0472 (13)	−0.0007 (10)	−0.0031 (10)	−0.0046 (10)
C14	0.0399 (16)	0.0565 (19)	0.077 (2)	0.0120 (14)	0.0149 (15)	0.0303 (16)
C15	0.0522 (18)	0.063 (2)	0.0633 (18)	0.0242 (15)	0.0275 (15)	0.0178 (15)
C16	0.0483 (18)	0.073 (2)	0.074 (2)	0.0206 (16)	0.0344 (16)	0.0345 (18)

S1—O2	1.4316 (18)	C6—H6A	0.9800
S1—O1	1.4351 (17)	C6—H6B	0.9800
S1—N3	1.644 (2)	C6—H6C	0.9800
S1—C7	1.748 (2)	C7—C12	1.392 (3)
O3—C14	1.439 (3)	C7—C8	1.396 (3)
O3—C13	1.442 (3)	C8—C9	1.379 (3)
N1—C1	1.334 (3)	C8—H8	0.9500
N1—C2	1.353 (3)	C9—C10	1.407 (3)
N2—C1	1.340 (3)	C9—H9	0.9500
N2—C4	1.346 (3)	C10—C11	1.405 (3)
N3—C1	1.394 (3)	C11—C12	1.377 (3)
N3—H3N	0.8800	C11—H11	0.9500
N4—C10	1.377 (3)	C12—H12	0.9500
N4—C13	1.420 (3)	C13—C16	1.494 (4)
N4—H4N	0.8800	C13—H13	1.0000
C2—C3	1.384 (3)	C14—C15	1.488 (4)
C2—C5	1.500 (3)	C14—H14A	0.9900
C3—C4	1.386 (3)	C14—H14B	0.9900
C3—H3	0.9500	C15—C16	1.523 (4)
C4—C6	1.490 (3)	C15—H15A	0.9900
C5—H5A	0.9800	C15—H15B	0.9900
C5—H5B	0.9800	C16—H16A	0.9900
C5—H5C	0.9800	C16—H16B	0.9900
O2—S1—O1	119.23 (10)	C8—C7—S1	121.15 (17)
O2—S1—N3	109.23 (10)	C9—C8—C7	120.0 (2)
O1—S1—N3	102.72 (10)	C9—C8—H8	120.0
O2—S1—C7	108.79 (11)	C7—C8—H8	120.0
O1—S1—C7	108.43 (10)	C8—C9—C10	120.7 (2)
N3—S1—C7	107.85 (10)	C8—C9—H9	119.6
C14—O3—C13	107.26 (19)	C10—C9—H9	119.6
C1—N1—C2	115.27 (19)	N4—C10—C11	122.3 (2)
C1—N2—C4	115.51 (18)	N4—C10—C9	118.9 (2)
C1—N3—S1	125.67 (16)	C11—C10—C9	118.6 (2)
C1—N3—H3N	116.9	C12—C11—C10	120.4 (2)
S1—N3—H3N	115.6	C12—C11—H11	119.8
C10—N4—C13	124.3 (2)	C10—C11—H11	119.8
C10—N4—H4N	119.7	C11—C12—C7	120.4 (2)
C13—N4—H4N	112.9	C11—C12—H12	119.8
N1—C1—N2	128.24 (19)	C7—C12—H12	119.8
N1—C1—N3	117.29 (19)	N4—C13—O3	108.7 (2)
N2—C1—N3	114.47 (18)	N4—C13—C16	116.1 (2)
N1—C2—C3	121.2 (2)	O3—C13—C16	103.8 (2)
N1—C2—C5	116.0 (2)	N4—C13—H13	109.3
C3—C2—C5	122.79 (19)	O3—C13—H13	109.3
C2—C3—C4	118.66 (19)	C16—C13—H13	109.3
C2—C3—H3	120.7	O3—C14—C15	108.2 (2)
C4—C3—H3	120.7	O3—C14—H14A	110.1
N2—C4—C3	121.1 (2)	C15—C14—H14A	110.1
N2—C4—C6	116.5 (2)	O3—C14—H14B	110.1
C3—C4—C6	122.36 (19)	C15—C14—H14B	110.1
C2—C5—H5A	109.5	H14A—C14—H14B	108.4
C2—C5—H5B	109.5	C14—C15—C16	101.9 (2)
H5A—C5—H5B	109.5	C14—C15—H15A	111.4
C2—C5—H5C	109.5	C16—C15—H15A	111.4
H5A—C5—H5C	109.5	C14—C15—H15B	111.4
H5B—C5—H5C	109.5	C16—C15—H15B	111.4
C4—C6—H6A	109.5	H15A—C15—H15B	109.3
C4—C6—H6B	109.5	C13—C16—C15	101.4 (2)
H6A—C6—H6B	109.5	C13—C16—H16A	111.5
C4—C6—H6C	109.5	C15—C16—H16A	111.5
H6A—C6—H6C	109.5	C13—C16—H16B	111.5
H6B—C6—H6C	109.5	C15—C16—H16B	111.5
C12—C7—C8	119.9 (2)	H16A—C16—H16B	109.3
C12—C7—S1	118.99 (17)
O2—S1—N3—C1	56.4 (2)	N3—S1—C7—C8	95.14 (19)
O1—S1—N3—C1	−176.07 (18)	C12—C7—C8—C9	0.4 (3)
C7—S1—N3—C1	−61.7 (2)	S1—C7—C8—C9	−179.57 (16)
C2—N1—C1—N2	0.0 (3)	C7—C8—C9—C10	−0.1 (3)
C2—N1—C1—N3	179.72 (19)	C13—N4—C10—C11	−22.4 (4)
C4—N2—C1—N1	0.5 (3)	C13—N4—C10—C9	161.0 (2)
C4—N2—C1—N3	−179.25 (19)	C8—C9—C10—N4	176.2 (2)
S1—N3—C1—N1	1.0 (3)	C8—C9—C10—C11	−0.6 (3)
S1—N3—C1—N2	−179.18 (16)	N4—C10—C11—C12	−175.7 (2)
C1—N1—C2—C3	−0.2 (3)	C9—C10—C11—C12	0.9 (4)
C1—N1—C2—C5	179.3 (2)	C10—C11—C12—C7	−0.6 (4)
N1—C2—C3—C4	−0.1 (3)	C8—C7—C12—C11	0.0 (3)
C5—C2—C3—C4	−179.6 (2)	S1—C7—C12—C11	179.91 (18)
C1—N2—C4—C3	−0.8 (3)	C10—N4—C13—O3	−104.0 (3)
C1—N2—C4—C6	−179.43 (19)	C10—N4—C13—C16	139.5 (3)
C2—C3—C4—N2	0.6 (3)	C14—O3—C13—N4	−153.7 (2)
C2—C3—C4—C6	179.2 (2)	C14—O3—C13—C16	−29.5 (3)
O2—S1—C7—C12	156.85 (17)	C13—O3—C14—C15	5.4 (3)
O1—S1—C7—C12	25.8 (2)	O3—C14—C15—C16	20.2 (4)
N3—S1—C7—C12	−84.79 (19)	N4—C13—C16—C15	160.5 (3)
O2—S1—C7—C8	−23.2 (2)	O3—C13—C16—C15	41.3 (3)
O1—S1—C7—C8	−154.31 (18)	C14—C15—C16—C13	−37.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3n···O3i	0.88	1.98	2.854 (3)	174
N4—H4n···N2ii	0.88	2.22	3.086 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3n⋯O3i	0.88	1.98	2.854 (3)	174
N4—H4n⋯N2ii	0.88	2.22	3.086 (3)	167

Symmetry codes: (i) ; (ii) .