N-(4-Amino­pyrimidin-5-yl)-4-methyl-N-(4-methyl­phenyl­sulfon­yl)benzene­sulfonamide

Taher, A.; Smith, V.J.

doi:10.1107/S1600536812046442

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3362

doi:10.1107/S1600536812046442

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N-(4-Aminopyrimidin-5-yl)-4-methyl-N-(4-methylphenylsulfonyl)benzenesulfonamide

Abu Taher ^a ^* and Vincent J Smith ^a

^aDepartment of Chemistry and Polymer Science, University of Stellenbosch, Private Bag X1, Matieland 7602, South Africa
^*Correspondence e-mail: abut@sun.ac.za

(Received 15 October 2012; accepted 9 November 2012; online 17 November 2012)

In the title compound, C₁₈H₁₈N₄O₄S₂, the mean planes passing through the tosyl benzene rings form dihedral angles of 48.42 (9) and 15.1 (1)° with the aminopyrimidine ring. In the crystal, molecules associate via N—H⋯N and N—H⋯O hydrogen bonds, forming extended hydrogen-bonded sheets that lie parallel to the bc plane. The N—H⋯N hydrogen bonds propagate along the b-axis direction, while the N—H⋯O hydrogen bonds propagate along the c-axis direction.

Related literature

For the synthesis of related sulfonamides, see: Schetty (1969 ); Taher & Smith (2012 ). For applications of ring-closing metathesis (RCM) on sulfonamide-protected allyl-containing substrates, see: Yadav et al. (2011 ); Panayides et al. (2007a ,b ).

Experimental

Crystal data

C₁₈H₁₈N₄O₄S₂
M_r = 418.48
Monoclinic, C 2/c
a = 36.559 (9) Å
b = 6.9044 (18) Å
c = 15.524 (4) Å
β = 103.852 (3)°
V = 3804.6 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 103 K
0.13 × 0.13 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.962, T_max = 0.969
11288 measured reflections
4459 independent reflections
3156 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.116
S = 1.04
4459 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1ⁱ	0.88	2.16	3.036 (3)	178
N3—H3B⋯N1ⁱⁱ	0.88	2.30	2.986 (3)	135
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ; Atwood & Barbour, 2003 ); software used to prepare material for publication: X-SEED.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812046442/hg5262sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812046442/hg5262Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812046442/hg5262Isup3.cml

checkCIF report

Comment top

The para-toluene sulfonyl group (Ts) is frequently used as a protecting group for amines, particularly when monoalkylation of the amine is desired as the sulfonamide can then be cleaved in a subsequent step. The van Otterlo research group have successfully utilized the Ts group during their syntheses of annulated heterocycles using ring-closing metathesis (RCM) and isomerization strategies (see for example: Panayides et al., 2007a, 2007b; Yadav et al., 2011). In this present research the main aim was to synthesize pyrimidine-annulated heterocycles in which a 4,5-disulfonamide-protected 4,5-diaminopyrimidine was required. Surprisingly, instead of the desired 4,5-diTs compound the isomeric 5,5-disulfonamide-protected 4,5-diaminopyrimidine was obtained. It should be pointed out that according to literature it is uncommon for this type of ditosylation to occur on one amine in the presence of another amine group [see for instance Schetty (1969) and Taher et al. (2012)].

Related literature top

For the synthesis of related sulfonamides, see: Schetty (1969); Taher & Smith (2012). For applications of ring-closing metathesis (RCM) on sulfonamide-protected allyl-containing substrates, see: Yadav et al. (2011); Panayides et al. (2007a,b).

Experimental top

To an ice-cooled solution of 4,5-diaminopyrimidine (0.100 g, 0.908 mmol) in pyridine (10 ml), was slowly added 4-methylbenzene-1-sulfonyl chloride (0.380 g, 2.00 mmol). The mixture was then stirred at 273.15 K for 2 h. After completion of the reaction, as monitored by TLC, ice-cooled water (10 ml) was added to the reaction mixture. A white solid precipitate was formed which was collected by filteration and washed with dilute HCl (15 ml, 1 M) and plenty of water, after which it was dried in an oven (373.15 K). The residue was recrystallized from MeOH/CH₂Cl₂ to afford the product N-(4-aminopyrimidin-5-yl)-4-methyl-N-tosylbenzenesulfonamide as a colourless crystalline material (0.357 g, 94%).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001; Atwood & Barbour, 2003); software used to prepare material for publication: X-SEED (Barbour, 2001; Atwood & Barbour, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atomic numbering scheme - the displacement ellipsoids are shown at the 50 percent probability.
	Fig. 2. The hydrogen bonded sheet viewed along a and which runs parallel to the bc plane.
	Fig. 3. The hydrogen bond motif parallel to the bc plane.

N-(4-Aminopyrimidin-5-yl)-4-methyl-N-(4- methylphenylsulfonyl)benzenesulfonamide top

Crystal data top

C₁₈H₁₈N₄O₄S₂	F(000) = 1744
M_r = 418.48	D_x = 1.461 Mg m⁻³
Monoclinic, C2/c	Melting point: 211 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 36.559 (9) Å	Cell parameters from 2317 reflections
b = 6.9044 (18) Å	θ = 2.3–27.0°
c = 15.524 (4) Å	µ = 0.31 mm⁻¹
β = 103.852 (3)°	T = 103 K
V = 3804.6 (17) Å³	Prismatic, colourless
Z = 8	0.13 × 0.13 × 0.10 mm

Data collection top

Bruker SMART APEX CCD diffractometer	4459 independent reflections
Radiation source: fine-focus sealed tube, SMART APEX	3156 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 28.7°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −48→47
T_min = 0.962, T_max = 0.969	k = −5→8
11288 measured reflections	l = −19→20

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0545P)² + 0.5062P] where P = (F_o² + 2F_c²)/3
4459 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₁₈H₁₈N₄O₄S₂	V = 3804.6 (17) Å³
M_r = 418.48	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 36.559 (9) Å	µ = 0.31 mm⁻¹
b = 6.9044 (18) Å	T = 103 K
c = 15.524 (4) Å	0.13 × 0.13 × 0.10 mm
β = 103.852 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	4459 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3156 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.969	R_int = 0.041
11288 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.04	Δρ_max = 0.40 e Å⁻³
4459 reflections	Δρ_min = −0.58 e Å⁻³
254 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.089895 (16)	0.32905 (8)	0.29158 (4)	0.01860 (15)
S2	0.169329 (16)	0.42295 (8)	0.38027 (4)	0.01945 (15)
O1	0.10267 (4)	0.4335 (2)	0.22487 (10)	0.0232 (4)
O2	0.07469 (5)	0.1386 (2)	0.27300 (10)	0.0237 (4)
O3	0.19243 (4)	0.3605 (2)	0.46334 (10)	0.0249 (4)
O4	0.16212 (5)	0.6242 (2)	0.36298 (11)	0.0260 (4)
C4	0.12489 (6)	0.1827 (3)	0.44923 (14)	0.0165 (5)
C1	0.11889 (6)	0.2557 (3)	0.52950 (14)	0.0169 (5)
C12	0.18620 (6)	0.3219 (3)	0.29353 (14)	0.0186 (5)
N3	0.11439 (5)	0.4438 (3)	0.54561 (12)	0.0206 (4)
H3A	0.1104	0.4802	0.5969	0.025*
H3B	0.1155	0.5310	0.5049	0.025*
N4	0.12770 (5)	0.3096 (3)	0.37743 (11)	0.0176 (4)
N1	0.12518 (6)	−0.1406 (3)	0.50446 (13)	0.0223 (4)
C5	0.05758 (6)	0.4700 (3)	0.33053 (14)	0.0180 (5)
N2	0.11685 (5)	0.1306 (3)	0.59516 (12)	0.0205 (4)
C2	0.11992 (7)	−0.0559 (3)	0.57827 (15)	0.0225 (5)
H2	0.1182	−0.1417	0.6250	0.027*
C16	0.20041 (6)	0.3556 (4)	0.15198 (16)	0.0244 (5)
H16	0.2014	0.4328	0.1019	0.029*
C17	0.18700 (6)	0.4358 (4)	0.22029 (15)	0.0215 (5)
H17	0.1785	0.5662	0.2171	0.026*
C15	0.21246 (6)	0.1637 (4)	0.15541 (16)	0.0253 (5)
C3	0.12811 (6)	−0.0140 (3)	0.44085 (15)	0.0201 (5)
H3	0.1326	−0.0632	0.3872	0.024*
C10	0.06049 (7)	0.6690 (4)	0.32818 (18)	0.0288 (6)
H10	0.0806	0.7286	0.3089	0.035*
C8	0.00387 (7)	0.6964 (4)	0.38297 (16)	0.0270 (6)
C14	0.21133 (7)	0.0535 (4)	0.22965 (17)	0.0269 (6)
H14	0.2195	−0.0774	0.2327	0.032*
C6	0.02854 (7)	0.3822 (4)	0.35961 (16)	0.0253 (5)
H6	0.0270	0.2450	0.3618	0.030*
C13	0.19845 (7)	0.1310 (4)	0.29931 (16)	0.0243 (5)
H13	0.1980	0.0550	0.3500	0.029*
C7	0.00199 (7)	0.4962 (4)	0.38528 (16)	0.0252 (5)
H7	−0.0180	0.4362	0.4049	0.030*
C9	0.03359 (8)	0.7801 (4)	0.3544 (2)	0.0400 (7)
H9	0.0354	0.9173	0.3530	0.048*
C18	0.22614 (8)	0.0793 (5)	0.07884 (18)	0.0386 (7)
H18C	0.2518	0.1247	0.0818	0.058*
H18A	0.2094	0.1210	0.0227	0.058*
H18B	0.2260	−0.0623	0.0824	0.058*
C11	−0.02630 (8)	0.8178 (4)	0.4063 (2)	0.0414 (7)
H11A	−0.0205	0.9551	0.4011	0.062*	0.50
H11B	−0.0276	0.7898	0.4674	0.062*	0.50
H11C	−0.0506	0.7878	0.3658	0.062*	0.50
H11D	−0.0453	0.7333	0.4218	0.062*	0.50
H11E	−0.0382	0.8987	0.3554	0.062*	0.50
H11F	−0.0152	0.9007	0.4571	0.062*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0218 (3)	0.0156 (3)	0.0187 (3)	0.0002 (2)	0.0055 (2)	−0.0004 (2)
S2	0.0223 (3)	0.0153 (3)	0.0224 (3)	−0.0022 (2)	0.0086 (2)	−0.0016 (2)
O1	0.0266 (9)	0.0251 (9)	0.0195 (8)	0.0010 (7)	0.0088 (7)	0.0048 (7)
O2	0.0286 (9)	0.0155 (9)	0.0260 (9)	−0.0020 (7)	0.0048 (7)	−0.0040 (7)
O3	0.0234 (9)	0.0292 (10)	0.0221 (8)	−0.0024 (7)	0.0051 (7)	−0.0005 (7)
O4	0.0338 (10)	0.0132 (8)	0.0352 (9)	−0.0024 (7)	0.0163 (8)	−0.0023 (7)
C4	0.0196 (11)	0.0143 (11)	0.0168 (10)	0.0000 (9)	0.0067 (9)	0.0035 (9)
C1	0.0139 (10)	0.0157 (11)	0.0207 (11)	−0.0004 (9)	0.0033 (9)	0.0005 (9)
C12	0.0182 (11)	0.0169 (12)	0.0210 (11)	−0.0024 (9)	0.0054 (9)	−0.0012 (9)
N3	0.0313 (11)	0.0127 (10)	0.0196 (9)	0.0014 (8)	0.0100 (8)	−0.0006 (8)
N4	0.0199 (10)	0.0157 (10)	0.0182 (9)	−0.0003 (8)	0.0064 (8)	0.0017 (8)
N1	0.0280 (11)	0.0151 (10)	0.0255 (10)	0.0034 (8)	0.0098 (9)	0.0028 (8)
C5	0.0164 (11)	0.0180 (12)	0.0188 (11)	0.0013 (9)	0.0028 (9)	0.0005 (9)
N2	0.0238 (10)	0.0153 (10)	0.0233 (10)	0.0012 (8)	0.0071 (8)	0.0026 (8)
C2	0.0265 (13)	0.0178 (12)	0.0242 (12)	0.0033 (10)	0.0081 (10)	0.0046 (10)
C16	0.0192 (12)	0.0326 (14)	0.0217 (12)	−0.0015 (10)	0.0055 (10)	0.0009 (10)
C17	0.0194 (12)	0.0204 (12)	0.0253 (12)	−0.0009 (10)	0.0067 (10)	0.0008 (10)
C15	0.0163 (11)	0.0343 (15)	0.0252 (12)	0.0001 (11)	0.0048 (10)	−0.0075 (11)
C3	0.0234 (12)	0.0177 (12)	0.0209 (11)	0.0011 (10)	0.0084 (10)	0.0003 (9)
C10	0.0248 (13)	0.0190 (13)	0.0458 (15)	0.0006 (10)	0.0145 (12)	0.0026 (11)
C8	0.0241 (13)	0.0261 (14)	0.0316 (13)	0.0073 (11)	0.0082 (11)	0.0027 (11)
C14	0.0233 (13)	0.0216 (13)	0.0362 (14)	0.0042 (10)	0.0080 (11)	−0.0040 (11)
C6	0.0304 (14)	0.0163 (12)	0.0315 (13)	−0.0025 (10)	0.0120 (11)	−0.0014 (10)
C13	0.0245 (13)	0.0225 (13)	0.0271 (12)	0.0037 (10)	0.0083 (11)	0.0023 (10)
C7	0.0214 (12)	0.0279 (14)	0.0285 (13)	−0.0011 (10)	0.0102 (10)	0.0004 (11)
C9	0.0406 (17)	0.0145 (13)	0.072 (2)	0.0056 (12)	0.0268 (16)	0.0037 (13)
C18	0.0290 (15)	0.057 (2)	0.0314 (14)	0.0093 (14)	0.0101 (12)	−0.0127 (14)
C11	0.0361 (16)	0.0362 (17)	0.0574 (19)	0.0130 (13)	0.0223 (15)	0.0070 (14)

Geometric parameters (Å, º) top

S1—O1	1.4291 (16)	C17—H17	0.9500
S1—O2	1.4299 (17)	C15—C14	1.390 (3)
S1—N4	1.6800 (19)	C15—C18	1.512 (3)
S1—C5	1.747 (2)	C3—H3	0.9500
S2—O4	1.4275 (17)	C10—C9	1.383 (3)
S2—O3	1.4284 (17)	C10—H10	0.9500
S2—N4	1.703 (2)	C8—C7	1.385 (3)
S2—C12	1.755 (2)	C8—C9	1.393 (4)
C4—C3	1.372 (3)	C8—C11	1.497 (3)
C4—C1	1.409 (3)	C14—C13	1.386 (3)
C4—N4	1.441 (3)	C14—H14	0.9500
C1—N3	1.340 (3)	C6—C7	1.381 (3)
C1—N2	1.352 (3)	C6—H6	0.9500
C12—C13	1.388 (3)	C13—H13	0.9500
C12—C17	1.388 (3)	C7—H7	0.9500
N3—H3A	0.8800	C9—H9	0.9500
N3—H3B	0.8800	C18—H18C	0.9800
N1—C2	1.340 (3)	C18—H18A	0.9800
N1—C3	1.342 (3)	C18—H18B	0.9800
C5—C10	1.379 (3)	C11—H11A	0.9800
C5—C6	1.389 (3)	C11—H11B	0.9800
N2—C2	1.324 (3)	C11—H11C	0.9800
C2—H2	0.9500	C11—H11D	0.9800
C16—C17	1.386 (3)	C11—H11E	0.9800
C16—C15	1.393 (3)	C11—H11F	0.9800
C16—H16	0.9500

O1—S1—O2	119.77 (10)	C5—C10—H10	120.7
O1—S1—N4	105.41 (9)	C9—C10—H10	120.7
O2—S1—N4	107.02 (10)	C7—C8—C9	118.0 (2)
O1—S1—C5	109.58 (10)	C7—C8—C11	120.5 (2)
O2—S1—C5	108.65 (11)	C9—C8—C11	121.4 (2)
N4—S1—C5	105.43 (10)	C13—C14—C15	121.2 (2)
O4—S2—O3	120.40 (10)	C13—C14—H14	119.4
O4—S2—N4	108.59 (10)	C15—C14—H14	119.4
O3—S2—N4	102.50 (9)	C7—C6—C5	119.3 (2)
O4—S2—C12	109.01 (11)	C7—C6—H6	120.3
O3—S2—C12	109.41 (10)	C5—C6—H6	120.3
N4—S2—C12	105.89 (10)	C14—C13—C12	118.7 (2)
C3—C4—C1	118.2 (2)	C14—C13—H13	120.6
C3—C4—N4	120.34 (19)	C12—C13—H13	120.6
C1—C4—N4	121.43 (19)	C6—C7—C8	121.3 (2)
N3—C1—N2	116.58 (19)	C6—C7—H7	119.4
N3—C1—C4	124.3 (2)	C8—C7—H7	119.4
N2—C1—C4	119.1 (2)	C10—C9—C8	121.8 (2)
C13—C12—C17	121.4 (2)	C10—C9—H9	119.1
C13—C12—S2	119.69 (18)	C8—C9—H9	119.1
C17—C12—S2	118.92 (18)	C15—C18—H18C	109.5
C1—N3—H3A	120.0	C15—C18—H18A	109.5
C1—N3—H3B	120.0	H18C—C18—H18A	109.5
H3A—N3—H3B	120.0	C15—C18—H18B	109.5
C4—N4—S1	117.70 (15)	H18C—C18—H18B	109.5
C4—N4—S2	119.23 (15)	H18A—C18—H18B	109.5
S1—N4—S2	122.98 (11)	C8—C11—H11A	109.5
C2—N1—C3	113.4 (2)	C8—C11—H11B	109.5
C10—C5—C6	120.9 (2)	H11A—C11—H11B	109.5
C10—C5—S1	118.89 (18)	C8—C11—H11C	109.5
C6—C5—S1	120.14 (18)	H11A—C11—H11C	109.5
C2—N2—C1	116.72 (19)	H11B—C11—H11C	109.5
N2—C2—N1	129.0 (2)	C8—C11—H11D	109.5
N2—C2—H2	115.5	H11A—C11—H11D	141.1
N1—C2—H2	115.5	H11B—C11—H11D	56.3
C17—C16—C15	121.1 (2)	H11C—C11—H11D	56.3
C17—C16—H16	119.4	C8—C11—H11E	109.5
C15—C16—H16	119.4	H11A—C11—H11E	56.3
C16—C17—C12	118.8 (2)	H11B—C11—H11E	141.1
C16—C17—H17	120.6	H11C—C11—H11E	56.3
C12—C17—H17	120.6	H11D—C11—H11E	109.5
C14—C15—C16	118.7 (2)	C8—C11—H11F	109.5
C14—C15—C18	121.4 (2)	H11A—C11—H11F	56.3
C16—C15—C18	119.8 (2)	H11B—C11—H11F	56.3
N1—C3—C4	123.4 (2)	H11C—C11—H11F	141.1
N1—C3—H3	118.3	H11D—C11—H11F	109.5
C4—C3—H3	118.3	H11E—C11—H11F	109.5
C5—C10—C9	118.7 (2)

C3—C4—C1—N3	−178.4 (2)	O2—S1—C5—C6	16.1 (2)
N4—C4—C1—N3	1.7 (3)	N4—S1—C5—C6	−98.4 (2)
C3—C4—C1—N2	0.5 (3)	N3—C1—N2—C2	177.6 (2)
N4—C4—C1—N2	−179.33 (19)	C4—C1—N2—C2	−1.4 (3)
O4—S2—C12—C13	174.23 (18)	C1—N2—C2—N1	0.6 (4)
O3—S2—C12—C13	40.7 (2)	C3—N1—C2—N2	1.0 (4)
N4—S2—C12—C13	−69.1 (2)	C15—C16—C17—C12	0.9 (3)
O4—S2—C12—C17	−5.7 (2)	C13—C12—C17—C16	−0.1 (3)
O3—S2—C12—C17	−139.28 (18)	S2—C12—C17—C16	179.89 (17)
N4—S2—C12—C17	110.92 (19)	C17—C16—C15—C14	−0.9 (3)
C3—C4—N4—S1	78.1 (2)	C17—C16—C15—C18	178.7 (2)
C1—C4—N4—S1	−102.1 (2)	C2—N1—C3—C4	−1.9 (3)
C3—C4—N4—S2	−98.7 (2)	C1—C4—C3—N1	1.2 (3)
C1—C4—N4—S2	81.1 (2)	N4—C4—C3—N1	−178.9 (2)
O1—S1—N4—C4	−169.87 (15)	C6—C5—C10—C9	−0.8 (4)
O2—S1—N4—C4	−41.33 (18)	S1—C5—C10—C9	176.4 (2)
C5—S1—N4—C4	74.23 (18)	C16—C15—C14—C13	0.1 (4)
O1—S1—N4—S2	6.80 (15)	C18—C15—C14—C13	−179.4 (2)
O2—S1—N4—S2	135.34 (13)	C10—C5—C6—C7	0.9 (4)
C5—S1—N4—S2	−109.10 (14)	S1—C5—C6—C7	−176.23 (18)
O4—S2—N4—C4	−130.54 (16)	C15—C14—C13—C12	0.6 (4)
O3—S2—N4—C4	−2.12 (18)	C17—C12—C13—C14	−0.7 (3)
C12—S2—N4—C4	112.52 (17)	S2—C12—C13—C14	179.38 (18)
O4—S2—N4—S1	52.84 (15)	C5—C6—C7—C8	−0.3 (4)
O3—S2—N4—S1	−178.74 (12)	C9—C8—C7—C6	−0.4 (4)
C12—S2—N4—S1	−64.10 (15)	C11—C8—C7—C6	176.7 (2)
O1—S1—C5—C10	−28.6 (2)	C5—C10—C9—C8	0.0 (4)
O2—S1—C5—C10	−161.14 (19)	C7—C8—C9—C10	0.6 (4)
N4—S1—C5—C10	84.4 (2)	C11—C8—C9—C10	−176.5 (3)
O1—S1—C5—C6	148.63 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.88	2.16	3.036 (3)	178
N3—H3B···N1ⁱⁱ	0.88	2.30	2.986 (3)	135

Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₄O₄S₂
M_r	418.48
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	103
a, b, c (Å)	36.559 (9), 6.9044 (18), 15.524 (4)
β (°)	103.852 (3)
V (Å³)	3804.6 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.13 × 0.13 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.962, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	11288, 4459, 3156
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.116, 1.04
No. of reflections	4459
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.58

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001; Atwood & Barbour, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.88	2.16	3.036 (3)	178
N3—H3B···N1ⁱⁱ	0.88	2.30	2.986 (3)	135

Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, y+1, z.

Acknowledgements

AT thanks the National Research Foundation (NRF), Pretoria, for providing an Innovation Fellowship and Professor W. A. L. van Otterlo for his research oversight. Stellenbosch University's Science Faculty is also acknowledged for providing the laboratory space and addition financial research support.

References

Atwood, J. L. & Barbour, L. J. (2003). Cryst. Growth. Des. 3, 3–8. Web of Science CrossRef CAS Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Panayides, J.-L., Pathak, R., de Koning, C. B. & van Otterlo, W. A. L. (2007a). Eur. J. Org. Chem. pp. 4953–4961. Web of Science CrossRef Google Scholar
Panayides, J.-L., Pathak, R., Panagiotopoulos, H., Davids, H., Fernandes, M. A., de Koning, C. B. & van Otterlo, W. A. L. (2007b). Tetrahedron, 63, 4737–4747. Web of Science CSD CrossRef CAS Google Scholar
Schetty, G. (1969). Helv. Chim. Acta, 52, 1796–1802. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Taher, A. & Smith, V. J. (2012). Acta Cryst. E68, o1136. CSD CrossRef IUCr Journals Google Scholar
Yadav, D. B., Morgans, G. L., Aderibigbe, B. A., Madeley, L. G., Fernandes, M. A., Michael, J. P., de Koning, C. B. & van Otterlo, W. A. L. (2011). Tetrahedron, 67, 2991–2997. Web of Science CSD CrossRef CAS Google Scholar

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Volume 68| Part 12| December 2012| Page o3362

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-(4-Amino­pyrimidin-5-yl)-4-methyl-N-(4-methyl­phenyl­sulfon­yl)benzene­sulfonamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

N-(4-Aminopyrimidin-5-yl)-4-methyl-N-(4-methylphenylsulfonyl)benzenesulfonamide