N-(p-Tolyl-sulfon-yl)-l-asparagine.

In the title compound, C(11)H(14)N(2)O(5)S, the amide O atom acts as a hydrogen-bond acceptor from a carboxyl-ate O atom and a secondary amino N atom. In addition, one of the sulfonyl O atoms and the carbonyl O atom of the carboxyl group also form hydrogen bonds with the primary amido N atom. These intermolecular hydrogen-bonding inter-actions give rise to a layer structure, with the layers parallel to the ac plane.

Related literature

For the anti­bacterial and anti­cancer activity of l-asparagines, Wagastuma et al. (1983 ▶); Murphy & Stubbins (1980 ▶). For a related compound, see Arshad et al. (2009 ▶).

Experimental

Crystal data

C11H14N2O5S

M = 286.30

Orthorhombic,

a = 8.7566 (6) Å

b = 22.900 (2) Å

c = 6.9692 (7) Å

V = 1397.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.37 × 0.11 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.914, T max = 0.983

8388 measured reflections

3206 independent reflections

2451 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.099

S = 1.02

3206 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 1338 Friedel pairs

Flack parameter: −0.03 (8)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810004034/bv2133sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004034/bv2133Isup2.hkl

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

C11H14N2O5S	F(000) = 600
Mr = 286.30	Dx = 1.361 Mg m−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 2600 reflections
a = 8.7566 (6) Å	θ = 2.5–24°
b = 22.900 (2) Å	µ = 0.25 mm−1
c = 6.9692 (7) Å	T = 296 K
V = 1397.5 (2) Å3	Block, white
Z = 4	0.37 × 0.11 × 0.07 mm

Bruker APEXII CCD area-detector diffractometer	3206 independent reflections
Radiation source: fine-focus sealed tube	2451 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.914, Tmax = 0.983	k = −26→29
8388 measured reflections	l = −9→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0521P)2 + ] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3206 reflections	Δρmax = 0.18 e Å−3
174 parameters	Δρmin = −0.27 e Å−3
0 restraints	Absolute structure: Flack (1983), 1328 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (8)

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.

	x	y	z	Uiso*/Ueq
S1	0.95716 (6)	0.62903 (3)	0.10823 (10)	0.04939 (18)
O1	0.9573 (2)	0.61117 (9)	−0.0862 (3)	0.0778 (6)
O2	1.09832 (17)	0.64258 (8)	0.2020 (3)	0.0636 (5)
O3	0.62170 (16)	0.68014 (8)	0.3996 (2)	0.0554 (4)
O4	0.76473 (19)	0.73119 (9)	0.6017 (2)	0.0629 (5)
H4	0.7019	0.7200	0.6808	0.094*
O5	1.08999 (14)	0.79700 (8)	0.1128 (2)	0.0493 (4)
N1	0.85411 (17)	0.68699 (8)	0.1208 (3)	0.0392 (4)
H1	0.7966	0.6960	0.0253	0.047*
N2	0.90525 (19)	0.82712 (9)	−0.0810 (3)	0.0522 (5)
H2A	0.9703	0.8367	−0.1680	0.063*
H2B	0.8093	0.8323	−0.1008	0.063*
C1	0.8685 (3)	0.57415 (11)	0.2442 (4)	0.0490 (6)
C2	0.8893 (3)	0.57211 (12)	0.4400 (4)	0.0619 (7)
H2	0.9511	0.5994	0.5013	0.074*
C3	0.8171 (4)	0.52899 (16)	0.5433 (5)	0.0807 (10)
H3	0.8303	0.5277	0.6757	0.097*
C4	0.7259 (4)	0.48771 (14)	0.4570 (6)	0.0796 (10)
C5	0.7061 (4)	0.49096 (16)	0.2613 (7)	0.0896 (11)
H5	0.6442	0.4637	0.2002	0.107*
C6	0.7762 (3)	0.53379 (13)	0.1549 (5)	0.0712 (9)
H6	0.7613	0.5355	0.0229	0.085*
C7	0.6559 (5)	0.43887 (16)	0.5732 (7)	0.1317 (18)
H7A	0.5955	0.4145	0.4908	0.198*
H7B	0.5921	0.4551	0.6719	0.198*
H7C	0.7355	0.4160	0.6309	0.198*
C8	0.8551 (2)	0.72435 (9)	0.2877 (3)	0.0357 (5)
H8	0.9551	0.7208	0.3497	0.043*
C9	0.7331 (2)	0.70850 (10)	0.4343 (3)	0.0375 (5)
C10	0.8332 (2)	0.78799 (10)	0.2275 (3)	0.0416 (5)
H10A	0.7319	0.7931	0.1735	0.050*
H10B	0.8420	0.8131	0.3389	0.050*
C11	0.9521 (2)	0.80490 (9)	0.0805 (3)	0.0362 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0400 (3)	0.0489 (3)	0.0592 (4)	0.0011 (3)	0.0150 (3)	−0.0021 (3)
O1	0.0992 (14)	0.0717 (13)	0.0624 (12)	0.0039 (11)	0.0320 (12)	−0.0157 (11)
O2	0.0324 (8)	0.0578 (11)	0.1005 (15)	0.0023 (7)	0.0067 (8)	0.0111 (11)
O3	0.0385 (8)	0.0806 (12)	0.0471 (9)	−0.0149 (8)	0.0005 (7)	0.0108 (10)
O4	0.0571 (10)	0.0946 (15)	0.0369 (9)	−0.0274 (9)	0.0162 (8)	−0.0073 (10)
O5	0.0301 (7)	0.0789 (12)	0.0388 (8)	−0.0034 (7)	−0.0020 (7)	0.0164 (10)
N1	0.0368 (8)	0.0467 (11)	0.0342 (9)	0.0025 (8)	0.0010 (8)	0.0005 (10)
N2	0.0325 (8)	0.0808 (15)	0.0432 (11)	0.0045 (9)	0.0011 (8)	0.0199 (11)
C1	0.0413 (11)	0.0409 (14)	0.0646 (16)	0.0019 (10)	0.0084 (11)	−0.0013 (13)
C2	0.0677 (16)	0.0459 (16)	0.072 (2)	−0.0084 (13)	−0.0039 (13)	0.0062 (14)
C3	0.096 (2)	0.067 (2)	0.079 (2)	−0.0022 (19)	0.0075 (17)	0.0203 (19)
C4	0.074 (2)	0.046 (2)	0.119 (3)	−0.0002 (16)	0.0206 (19)	0.017 (2)
C5	0.076 (2)	0.059 (2)	0.134 (3)	−0.0230 (16)	0.006 (2)	−0.010 (2)
C6	0.0749 (18)	0.0609 (19)	0.078 (2)	−0.0156 (16)	0.0060 (15)	−0.0088 (17)
C7	0.127 (3)	0.074 (3)	0.195 (5)	−0.013 (2)	0.033 (4)	0.059 (3)
C8	0.0277 (9)	0.0456 (13)	0.0338 (11)	−0.0016 (9)	0.0021 (8)	0.0037 (10)
C9	0.0315 (9)	0.0479 (14)	0.0332 (11)	0.0011 (9)	0.0000 (8)	0.0078 (10)
C10	0.0390 (11)	0.0457 (14)	0.0400 (12)	0.0033 (10)	0.0086 (9)	0.0032 (11)
C11	0.0339 (9)	0.0393 (11)	0.0353 (11)	−0.0010 (9)	0.0012 (9)	0.0021 (10)

S1—O1	1.416 (2)	C3—C4	1.376 (5)
S1—O2	1.4322 (18)	C3—H3	0.9300
S1—N1	1.6074 (18)	C4—C5	1.377 (5)
S1—C1	1.755 (3)	C4—C7	1.511 (4)
O3—C9	1.197 (2)	C5—C6	1.374 (5)
O4—C9	1.307 (2)	C5—H5	0.9300
O4—H4	0.8200	C6—H6	0.9300
O5—C11	1.242 (2)	C7—H7A	0.9600
N1—C8	1.444 (3)	C7—H7B	0.9600
N1—H1	0.8600	C7—H7C	0.9600
N2—C11	1.302 (3)	C8—C9	1.522 (3)
N2—H2A	0.8600	C8—C10	1.529 (3)
N2—H2B	0.8600	C8—H8	0.9800
C1—C6	1.376 (4)	C10—C11	1.511 (3)
C1—C2	1.378 (4)	C10—H10A	0.9700
C2—C3	1.376 (4)	C10—H10B	0.9700
C2—H2	0.9300
O1—S1—O2	119.92 (11)	C5—C6—C1	119.8 (3)
O1—S1—N1	106.93 (11)	C5—C6—H6	120.1
O2—S1—N1	106.30 (10)	C1—C6—H6	120.1
O1—S1—C1	108.07 (13)	C4—C7—H7A	109.5
O2—S1—C1	106.91 (12)	C4—C7—H7B	109.5
N1—S1—C1	108.27 (10)	H7A—C7—H7B	109.5
C9—O4—H4	109.5	C4—C7—H7C	109.5
C8—N1—S1	122.00 (14)	H7A—C7—H7C	109.5
C8—N1—H1	119.0	H7B—C7—H7C	109.5
S1—N1—H1	119.0	N1—C8—C9	113.27 (17)
C11—N2—H2A	120.0	N1—C8—C10	110.06 (17)
C11—N2—H2B	120.0	C9—C8—C10	108.87 (17)
H2A—N2—H2B	120.0	N1—C8—H8	108.2
C6—C1—C2	120.2 (3)	C9—C8—H8	108.2
C6—C1—S1	119.8 (2)	C10—C8—H8	108.2
C2—C1—S1	120.0 (2)	O3—C9—O4	124.65 (19)
C3—C2—C1	118.8 (3)	O3—C9—C8	124.49 (19)
C3—C2—H2	120.6	O4—C9—C8	110.84 (17)
C1—C2—H2	120.6	C11—C10—C8	110.12 (17)
C4—C3—C2	122.1 (3)	C11—C10—H10A	109.6
C4—C3—H3	119.0	C8—C10—H10A	109.6
C2—C3—H3	119.0	C11—C10—H10B	109.6
C3—C4—C5	118.0 (3)	C8—C10—H10B	109.6
C3—C4—C7	120.7 (4)	H10A—C10—H10B	108.2
C5—C4—C7	121.3 (4)	O5—C11—N2	121.34 (19)
C6—C5—C4	121.1 (3)	O5—C11—C10	120.65 (19)
C6—C5—H5	119.4	N2—C11—C10	118.00 (17)
C4—C5—H5	119.4
O1—S1—N1—C8	−166.24 (16)	C7—C4—C5—C6	−176.8 (3)
O2—S1—N1—C8	−37.03 (17)	C4—C5—C6—C1	0.3 (5)
C1—S1—N1—C8	77.52 (17)	C2—C1—C6—C5	−0.7 (4)
O1—S1—C1—C6	−19.0 (3)	S1—C1—C6—C5	−179.7 (3)
O2—S1—C1—C6	−149.3 (2)	S1—N1—C8—C9	−91.79 (18)
N1—S1—C1—C6	96.5 (2)	S1—N1—C8—C10	146.07 (15)
O1—S1—C1—C2	162.1 (2)	N1—C8—C9—O3	−19.7 (3)
O2—S1—C1—C2	31.7 (3)	C10—C8—C9—O3	103.1 (2)
N1—S1—C1—C2	−82.4 (2)	N1—C8—C9—O4	161.76 (19)
C6—C1—C2—C3	0.3 (4)	C10—C8—C9—O4	−75.4 (2)
S1—C1—C2—C3	179.3 (2)	N1—C8—C10—C11	−54.8 (2)
C1—C2—C3—C4	0.5 (5)	C9—C8—C10—C11	−179.54 (17)
C2—C3—C4—C5	−1.0 (5)	C8—C10—C11—O5	−53.0 (3)
C2—C3—C4—C7	176.4 (3)	C8—C10—C11—N2	126.1 (2)
C3—C4—C5—C6	0.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5i	0.82	1.78	2.592 (2)	168
N1—H1···O5ii	0.86	2.06	2.852 (2)	154
N2—H2A···O3iii	0.86	2.12	2.924 (2)	155
N2—H2B···O2ii	0.86	2.06	2.901 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O5i	0.82	1.78	2.592 (2)	168
N1—H1⋯O5ii	0.86	2.06	2.852 (2)	154
N2—H2A⋯O3iii	0.86	2.12	2.924 (2)	155
N2—H2B⋯O2ii	0.86	2.06	2.901 (2)	166

Symmetry codes: (i) ; (ii) ; (iii) .